#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:38:03 +0300 (Tue, 05 May 2020) $
#$Revision: 251540 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/61/7126144.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_7126144
loop_
_publ_author_name
'Shan, Xiang-Huan'
'Yang, Bo'
'Qu, Jian-Ping'
'Kang, Yan-Biao'
_publ_section_title
;
 CuSO₄-Catalyzed dual annulation to synthesize O, S or
 N-containing tetracyclic heteroacenes.
;
_journal_issue                   29
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4063
_journal_page_last               4066
_journal_paper_doi               10.1039/d0cc01172j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H8 Cl N O'
_chemical_formula_sum            'C14 H8 Cl N O'
_chemical_formula_weight         241.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-11 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.7356(3)
_cell_length_b                   5.75805(13)
_cell_length_c                   24.9630(5)
_cell_measurement_reflns_used    3319
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      73.8480
_cell_measurement_theta_min      6.0140
_cell_volume                     2118.07(8)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.541
_exptl_absorpt_coefficient_mu    3.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0379
_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)+(0.0550P)²+0.6299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             2073
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01172j2.cif
_cod_data_source_block           y-3-37
_cod_depositor_comments
'Adding full bibliography for 7126144--7126145.cif.'
_cod_original_cell_volume        2118.07(7)
_cod_database_code               7126144
_shelxl_version_number           2013-4
_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   0.584
_shelx_estimated_absorpt_t_min   0.544
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C6(H6), C14(H14), C12(H12), C13(H13), C2(H2), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.66872(3) -0.19185(8) 0.49426(2) 0.05202(18) Uani 1 1 d . . . . .
O1 O 0.67348(7) -0.05669(19) 0.73678(4) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.57331(8) 0.4169(2) 0.67373(5) 0.0358(3) Uani 1 1 d . . . . .
H1 H 0.5472 0.5502 0.6759 0.043 Uiso 1 1 calc R . . . .
C8 C 0.60548(9) 0.2870(3) 0.71573(6) 0.0323(3) Uani 1 1 d . . . . .
C10 C 0.65166(9) 0.0619(3) 0.78335(6) 0.0332(3) Uani 1 1 d . . . . .
C11 C 0.66894(10) -0.0180(3) 0.83442(6) 0.0382(4) Uani 1 1 d . . . . .
H11 H 0.6977 -0.1594 0.8403 0.046 Uiso 1 1 calc R . . . .
C6 C 0.66096(10) -0.0714(3) 0.59864(6) 0.0351(3) Uani 1 1 d . . . . .
H6 H 0.6914 -0.2093 0.6058 0.042 Uiso 1 1 calc R . . . .
C14 C 0.58180(10) 0.4144(3) 0.81629(6) 0.0362(3) Uani 1 1 d . . . . .
H14 H 0.5533 0.5565 0.8107 0.043 Uiso 1 1 calc R . . . .
C4 C 0.59064(9) 0.2934(3) 0.62720(6) 0.0340(3) Uani 1 1 d . . . . .
C12 C 0.64136(11) 0.1225(3) 0.87655(6) 0.0413(4) Uani 1 1 d . . . . .
H12 H 0.6519 0.0742 0.9115 0.050 Uiso 1 1 calc R . . . .
C7 C 0.64355(9) 0.0887(3) 0.69660(6) 0.0328(3) Uani 1 1 d . . . . .
C1 C 0.63833(10) -0.0095(3) 0.54702(6) 0.0383(3) Uani 1 1 d . . . . .
C13 C 0.59816(11) 0.3348(3) 0.86762(6) 0.0414(4) Uani 1 1 d . . . . .
H13 H 0.5801 0.4242 0.8967 0.050 Uiso 1 1 calc R . . . .
C5 C 0.63638(9) 0.0813(3) 0.63989(6) 0.0317(3) Uani 1 1 d . . . . .
C9 C 0.60893(9) 0.2771(3) 0.77309(6) 0.0312(3) Uani 1 1 d . . . . .
C2 C 0.59272(11) 0.1963(3) 0.53479(6) 0.0434(4) Uani 1 1 d . . . . .
H2 H 0.5782 0.2301 0.4994 0.052 Uiso 1 1 calc R . . . .
C3 C 0.56914(11) 0.3494(3) 0.57465(6) 0.0416(4) Uani 1 1 d . . . . .
H3 H 0.5394 0.4875 0.5666 0.050 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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 O1 C10 103.69(11) . . ?
C8 N1 C4 107.28(12) . . ?
N1 C8 C9 142.81(14) . . ?
C7 C8 N1 109.40(13) . . ?
C7 C8 C9 107.65(13) . . ?
O1 C10 C9 112.54(12) . . ?
C11 C10 O1 124.61(14) . . ?
C11 C10 C9 122.85(14) . . ?
C10 C11 C12 116.87(15) . . ?
C1 C6 C5 117.53(14) . . ?
C13 C14 C9 118.59(14) . . ?
N1 C4 C5 109.84(13) . . ?
N1 C4 C3 129.15(14) . . ?
C3 C4 C5 121.00(14) . . ?
C11 C12 C13 121.53(15) . . ?
O1 C7 C5 136.95(13) . . ?
C8 C7 O1 112.74(13) . . ?
C8 C7 C5 110.16(13) . . ?
C6 C1 Cl1 119.25(13) . . ?
C6 C1 C2 122.72(15) . . ?
C2 C1 Cl1 118.02(12) . . ?
C14 C13 C12 121.21(15) . . ?
C6 C5 C4 119.66(13) . . ?
C6 C5 C7 137.03(14) . . ?
C7 C5 C4 103.31(13) . . ?
C10 C9 C8 103.38(13) . . ?
C14 C9 C8 137.65(14) . . ?
C14 C9 C10 118.96(13) . . ?
C3 C2 C1 120.52(15) . . ?
C2 C3 C4 118.56(15) . . ?
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 C1 1.7430(16) . ?
O1 C10 1.3862(18) . ?
O1 C7 1.3789(18) . ?
N1 C8 1.3725(19) . ?
N1 C4 1.3854(19) . ?
C8 C7 1.359(2) . ?
C8 C9 1.434(2) . ?
C10 C11 1.379(2) . ?
C10 C9 1.413(2) . ?
C11 C12 1.388(2) . ?
C6 C1 1.378(2) . ?
C6 C5 1.402(2) . ?
C14 C13 1.382(2) . ?
C14 C9 1.396(2) . ?
C4 C5 1.430(2) . ?
C4 C3 1.387(2) . ?
C12 C13 1.396(2) . ?
C7 C5 1.420(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.374(2) . ?
