#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:36:55 +0200 (mar 06 de oct de 2020) $
#$Revision: 257878 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/98/7059873.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_7059873
loop_
_publ_author_name
'Shi, Yang'
'Wang, Gangqiang'
'Wang, Hang'
'Deng, Bin'
'Gao, Tao'
'Wang, Jian'
'Guo, Haibing'
'Wu, Minghu'
'Sun, Shaofa'
_publ_section_title
;
 Cu-catalyzed cyclization to construct indoles from
 N-(ortho-chloromethyl)aryl carbamates and terminal alkynes via a one-pot
 reaction
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14477
_journal_page_last               14480
_journal_paper_doi               10.1039/D0NJ01981J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 Cl N O2'
_chemical_formula_sum            'C18 H16 Cl N O2'
_chemical_formula_weight         313.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-08
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.04.02 svn.r1fbe7b6f for OlexSys, GUI svn.r6076)
;
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                100.487(8)
_cell_angle_beta                 104.790(7)
_cell_angle_gamma                106.520(8)
_cell_formula_units_Z            2
_cell_length_a                   7.3932(6)
_cell_length_b                   10.0477(10)
_cell_length_c                   11.2604(10)
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0750
_cell_measurement_theta_min      3.0230
_cell_volume                     745.56(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  40.00   1.00    1.00    --   11.74 -57.00 150.00  100
  2  ω    -21.00  88.00   1.00    1.00    --   11.74  77.00  60.00  109
  3  ω    -16.00  85.00   1.00    1.00    --   11.74  57.00 -60.00  101
  4  ω     34.00  99.00   1.00    1.00    --   11.74-178.00 150.00   65
  5  ω    -16.00  23.00   1.00    1.00    --   11.74  57.00-180.00   39
  6  ω    -20.00  53.00   1.00    1.00    --   11.74 -99.00 -30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0982811000
_diffrn_orient_matrix_UB_12      -0.0506208000
_diffrn_orient_matrix_UB_13      -0.0302614000
_diffrn_orient_matrix_UB_21      -0.0390454000
_diffrn_orient_matrix_UB_22      0.0526527000
_diffrn_orient_matrix_UB_23      0.0225581000
_diffrn_orient_matrix_UB_31      -0.0043050000
_diffrn_orient_matrix_UB_32      0.0230069000
_diffrn_orient_matrix_UB_33      -0.0562680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8435
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0336
_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)+(0.0382P)²+0.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2354
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj01981j2.cif
_cod_data_source_block           33-2
_cod_depositor_comments
;Adding full bibliography for 7059872--7059873.cif.

 Adding full bibliography for 7059872--7059873.cif.
;
_cod_original_cell_volume        745.55(12)
_cod_database_code               7059873
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C14(H14), C5(H5), C3(H3), C11(H11), C13(H13), C2(H2), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2019-03-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.638
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 0.68047(6) 0.95723(4) 1.12245(4) 0.01825(14) Uani 1 1 d . . . . .
O2 O 0.41017(16) 0.68750(11) 0.51828(10) 0.0168(3) Uani 1 1 d . . . . .
O1 O 0.51765(17) 0.82082(12) 0.72285(10) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.33596(19) 0.57808(13) 0.66496(12) 0.0127(3) Uani 1 1 d . . . . .
C8 C 0.3336(2) 0.56385(17) 0.78774(14) 0.0127(3) Uani 1 1 d . . . . .
C10 C 0.6699(2) 0.72409(16) 0.95248(14) 0.0133(3) Uani 1 1 d . . . . .
C15 C 0.7910(2) 0.84789(17) 1.05074(14) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.2136(2) 0.44401(16) 0.57417(15) 0.0131(3) Uani 1 1 d . . . . .
C7 C 0.2173(2) 0.42814(17) 0.77522(15) 0.0141(3) Uani 1 1 d . . . . .
H7 H 0.191825 0.391576 0.841757 0.017 Uiso 1 1 calc R U . . .
C16 C 0.4303(2) 0.70765(17) 0.64169(15) 0.0142(3) Uani 1 1 d . . . . .
C4 C -0.0370(2) 0.16301(17) 0.44643(15) 0.0179(4) Uani 1 1 d . . . . .
H4 H -0.121060 0.068936 0.402006 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9976(2) 0.88821(18) 1.09494(15) 0.0177(4) Uani 1 1 d . . . . .
H14 H 1.074605 0.972568 1.159909 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1396(2) 0.34947(17) 0.64293(15) 0.0131(3) Uani 1 1 d . . . . .
C9 C 0.4443(2) 0.68244(17) 0.90889(15) 0.0144(3) Uani 1 1 d . . . . .
H9A H 0.396897 0.653378 0.976212 0.017 Uiso 1 1 calc R U . . .
H9B H 0.411747 0.767318 0.897876 0.017 Uiso 1 1 calc R U . . .
C5 C 0.0144(2) 0.20735(17) 0.57780(15) 0.0161(4) Uani 1 1 d . . . . .
H5 H -0.033593 0.143602 0.622268 0.019 Uiso 1 1 calc R U . . .
C3 C 0.0364(2) 0.25851(17) 0.37989(15) 0.0178(4) Uani 1 1 d . . . . .
H3 H -0.000201 0.226479 0.291446 0.021 Uiso 1 1 calc R U . . .
C11 C 0.7644(2) 0.63834(18) 0.90029(15) 0.0169(4) Uani 1 1 d . . . . .
H11 H 0.687884 0.554400 0.834767 0.020 Uiso 1 1 calc R U . . .
C13 C 1.0870(2) 0.80116(19) 1.04099(16) 0.0206(4) Uani 1 1 d . . . . .
H13 H 1.225124 0.826769 1.069649 0.025 Uiso 1 1 calc R U . . .
C2 C 0.1617(2) 0.39925(17) 0.44164(15) 0.0163(4) Uani 1 1 d . . . . .
H2 H 0.209765 0.461893 0.396330 0.020 Uiso 1 1 calc R U . . .
C17 C 0.4921(3) 0.81746(17) 0.48180(16) 0.0200(4) Uani 1 1 d . . . . .
H17A H 0.636384 0.855373 0.518720 0.024 Uiso 1 1 calc R U . . .
H17B H 0.440418 0.890863 0.512028 0.024 Uiso 1 1 calc R U . . .
C12 C 0.9707(2) 0.67560(19) 0.94408(16) 0.0206(4) Uani 1 1 d . . . . .
H12 H 1.030608 0.616410 0.908438 0.025 Uiso 1 1 calc R U . . .
C18 C 0.4312(3) 0.77681(19) 0.33872(16) 0.0233(4) Uani 1 1 d . . . . .
H18A H 0.288493 0.733897 0.303308 0.035 Uiso 1 1 calc R U . . .
H18B H 0.490379 0.708893 0.310295 0.035 Uiso 1 1 calc R U . . .
H18C H 0.475661 0.861616 0.311000 0.035 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'
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
C16 O2 C17 115.12(12) . . ?
C1 N1 C8 107.98(12) . . ?
C16 N1 C8 123.96(13) . . ?
C16 N1 C1 127.84(13) . . ?
N1 C8 C9 124.23(14) . . ?
C7 C8 N1 108.75(13) . . ?
C7 C8 C9 127.03(14) . . ?
C15 C10 C9 120.83(14) . . ?
C15 C10 C11 116.99(14) . . ?
C11 C10 C9 122.13(14) . . ?
C10 C15 Cl1 119.04(12) . . ?
C14 C15 Cl1 118.39(12) . . ?
C14 C15 C10 122.57(15) . . ?
C6 C1 N1 106.80(13) . . ?
C2 C1 N1 131.96(14) . . ?
C2 C1 C6 121.24(14) . . ?
C8 C7 H7 125.5 . . ?
C8 C7 C6 108.99(14) . . ?
C6 C7 H7 125.5 . . ?
O2 C16 N1 110.45(13) . . ?
O1 C16 O2 125.34(14) . . ?
O1 C16 N1 124.21(14) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.43(15) . . ?
C3 C4 H4 119.8 . . ?
C15 C14 H14 120.5 . . ?
C13 C14 C15 119.07(15) . . ?
C13 C14 H14 120.5 . . ?
C1 C6 C7 107.49(13) . . ?
C5 C6 C1 119.73(14) . . ?
C5 C6 C7 132.78(15) . . ?
C8 C9 C10 115.50(13) . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C4 C5 C6 119.01(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.92(15) . . ?
C2 C3 H3 119.0 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.44(15) . . ?
C12 C11 H11 119.3 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 119.97(15) . . ?
C12 C13 H13 120.0 . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.66(14) . . ?
C3 C2 H2 121.2 . . ?
O2 C17 H17A 110.3 . . ?
O2 C17 H17B 110.3 . . ?
O2 C17 C18 107.27(13) . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.95(16) . . ?
C13 C12 H12 120.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C15 1.7470(16) . ?
O2 C16 1.3302(19) . ?
O2 C17 1.4536(19) . ?
O1 C16 1.2034(19) . ?
N1 C8 1.4195(19) . ?
N1 C1 1.418(2) . ?
N1 C16 1.397(2) . ?
C8 C7 1.349(2) . ?
C8 C9 1.495(2) . ?
C10 C15 1.390(2) . ?
C10 C9 1.519(2) . ?
C10 C11 1.394(2) . ?
C15 C14 1.389(2) . ?
C1 C6 1.411(2) . ?
C1 C2 1.394(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.432(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(2) . ?
C4 C3 1.396(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(2) . ?
C6 C5 1.398(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.382(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.387(2) . ?
C2 H2 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.500(2) . ?
C12 H12 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
Cl1 C15 C14 C13 178.64(12) . . . . ?
N1 C8 C7 C6 -0.15(17) . . . . ?
N1 C8 C9 C10 -70.33(19) . . . . ?
N1 C1 C6 C7 0.39(16) . . . . ?
N1 C1 C6 C5 -179.46(13) . . . . ?
N1 C1 C2 C3 -179.83(15) . . . . ?
C8 N1 C1 C6 -0.48(16) . . . . ?
C8 N1 C1 C2 178.92(16) . . . . ?
C8 N1 C16 O2 179.03(13) . . . . ?
C8 N1 C16 O1 -0.7(2) . . . . ?
C8 C7 C6 C1 -0.15(17) . . . . ?
C8 C7 C6 C5 179.66(16) . . . . ?
C10 C15 C14 C13 -1.1(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C15 C10 C9 C8 169.01(14) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C15 C14 C13 C12 0.0(2) . . . . ?
C1 N1 C8 C7 0.39(16) . . . . ?
C1 N1 C8 C9 -179.75(14) . . . . ?
C1 N1 C16 O2 -7.2(2) . . . . ?
C1 N1 C16 O1 173.08(14) . . . . ?
C1 C6 C5 C4 -1.0(2) . . . . ?
C7 C8 C9 C10 109.50(18) . . . . ?
C7 C6 C5 C4 179.16(16) . . . . ?
C16 O2 C17 C18 -172.43(13) . . . . ?
C16 N1 C8 C7 175.24(14) . . . . ?
C16 N1 C8 C9 -4.9(2) . . . . ?
C16 N1 C1 C6 -175.07(14) . . . . ?
C16 N1 C1 C2 4.3(3) . . . . ?
C4 C3 C2 C1 -0.1(2) . . . . ?
C14 C13 C12 C11 0.8(2) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C9 C8 C7 C6 180.00(14) . . . . ?
C9 C10 C15 Cl1 -0.9(2) . . . . ?
C9 C10 C15 C14 178.76(14) . . . . ?
C9 C10 C11 C12 -177.90(14) . . . . ?
C5 C4 C3 C2 0.1(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C11 C10 C15 Cl1 -178.47(11) . . . . ?
C11 C10 C15 C14 1.2(2) . . . . ?
C11 C10 C9 C8 -13.6(2) . . . . ?
C2 C1 C6 C7 -179.09(14) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C17 O2 C16 O1 -4.0(2) . . . . ?
C17 O2 C16 N1 176.28(12) . . . . ?
