#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:46:03 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258122 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/10/7241012.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_7241012
loop_
_publ_author_name
'Jia, Qianfa'
'Lan, Yunfei'
'Ye, Xin'
'Lin, Yinhe'
'Ren, Qiao'
_publ_section_title
;
 Direct access to multi-functionalized benzenes via [4 + 2] annulation of
 α-cyano-β-methylenones and α,β-unsaturated aldehydes
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              29171
_journal_page_last               29174
_journal_paper_doi               10.1039/D0RA05251E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C26 H17 N O'
_chemical_formula_weight         359.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-10-01 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3409(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.10003(14)
_cell_length_b                   12.07847(16)
_cell_length_c                   26.6169(3)
_cell_measurement_temperature    293(2)
_cell_volume                     3878.90(8)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            70860
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.040
_diffrn_reflns_theta_min         4.021
_exptl_absorpt_coefficient_mu    0.583
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0611
_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)+(0.0827P)²+1.4719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6946
_reflns_number_total             7562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra05251e2.cif
_cod_data_source_block           2019-9-26
_cod_depositor_comments          'Adding full bibliography for 7241012.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241012
_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_min   0.767
_shelx_estimated_absorpt_t_max   0.835
_shelxl_version_number           2014-1
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C11 C 0.91733(13) 0.06057(13) 0.08068(6) 0.0405(3) Uani 1 1 d . . . . .
C8 C 0.86544(13) -0.14211(13) 0.06667(6) 0.0416(4) Uani 1 1 d . . . . .
C17 C 1.05616(13) -0.09007(13) 0.07714(6) 0.0417(4) Uani 1 1 d . . . . .
H17 H 1.1103 -0.0358 0.0825 0.050 Uiso 1 1 calc R U . . .
C52 C 1.18160(14) 0.10174(14) 0.17661(6) 0.0446(4) Uani 1 1 d . . . . .
H52 H 1.2205 0.0451 0.1622 0.054 Uiso 1 1 calc R U . . .
C10 C 0.94584(13) -0.05789(13) 0.07476(6) 0.0393(3) Uani 1 1 d . . . . .
C16 C 0.97882(16) 0.14183(15) 0.05826(7) 0.0500(4) Uani 1 1 d . . . . .
H16 H 1.0366 0.1212 0.0391 0.060 Uiso 1 1 calc R U . . .
C25 C 1.00812(14) -0.28215(13) 0.06570(7) 0.0440(4) Uani 1 1 d . . . . .
C18 C 1.08988(13) -0.19915(14) 0.07193(6) 0.0418(4) Uani 1 1 d . . . . .
C6 C 0.80694(14) -0.33925(14) 0.05403(7) 0.0475(4) Uani 1 1 d . . . . .
C43 C 1.15212(15) 0.29654(14) 0.18863(7) 0.0467(4) Uani 1 1 d . . . . .
C34 C 1.04279(14) 0.16089(15) 0.22958(6) 0.0462(4) Uani 1 1 d . . . . .
C45 C 1.21152(14) 0.21025(14) 0.16744(6) 0.0442(4) Uani 1 1 d . . . . .
C33 C 1.09629(14) 0.07347(14) 0.20632(6) 0.0435(4) Uani 1 1 d . . . . .
C31 C 0.95735(18) -0.08097(18) 0.20996(8) 0.0613(5) Uani 1 1 d . . . . .
H31 H 0.9000 -0.0296 0.2090 0.074 Uiso 1 1 calc R U . . .
C7 C 0.89571(13) -0.25388(13) 0.06309(6) 0.0424(4) Uani 1 1 d . . . . .
C9 C 0.74914(15) -0.11335(15) 0.05877(8) 0.0543(4) Uani 1 1 d . . . . .
C46 C 1.30926(15) 0.22907(15) 0.13780(7) 0.0484(4) Uani 1 1 d . . . . .
C36 C 1.06884(14) 0.27210(14) 0.22092(7) 0.0460(4) Uani 1 1 d . . . . .
C12 C 0.83281(16) 0.09398(16) 0.10968(7) 0.0524(4) Uani 1 1 d . . . . .
H12 H 0.7916 0.0412 0.1256 0.063 Uiso 1 1 calc R U . . .
C32 C 1.06684(15) -0.04515(15) 0.21103(6) 0.0474(4) Uani 1 1 d . . . . .
C26 C 1.04251(17) -0.39851(16) 0.05792(9) 0.0645(6) Uani 1 1 d . . . . .
H26 H 1.1045 -0.4050 0.0395 0.077 Uiso 1 1 calc R U . . .
C13 C 0.80932(19) 0.20508(18) 0.11516(9) 0.0653(5) Uani 1 1 d . . . . .
H13 H 0.7523 0.2265 0.1346 0.078 Uiso 1 1 calc R U . . .
C27 C 1.15048(19) -0.12494(16) 0.21305(7) 0.0576(5) Uani 1 1 d . . . . .
H27 H 1.2241 -0.1025 0.2142 0.069 Uiso 1 1 calc R U . . .
C37 C 1.00543(15) 0.36051(15) 0.24580(7) 0.0513(4) Uani 1 1 d . . . . .
C24 C 1.25826(16) -0.30780(17) 0.10341(8) 0.0602(5) Uani 1 1 d . . . . .
H24 H 1.2148 -0.3522 0.1226 0.072 Uiso 1 1 calc R U . . .
C15 C 0.95513(19) 0.25250(16) 0.06412(8) 0.0608(5) Uani 1 1 d . . . . .
H15 H 0.9972 0.3058 0.0491 0.073 Uiso 1 1 calc R U . . .
C14 C 0.8698(2) 0.28440(16) 0.09205(9) 0.0659(6) Uani 1 1 d . . . . .
H14 H 0.8528 0.3590 0.0954 0.079 Uiso 1 1 calc R U . . .
C19 C 1.21017(14) -0.22367(15) 0.07364(7) 0.0475(4) Uani 1 1 d . . . . .
N1 N 0.66509(18) -0.0837(2) 0.04960(11) 0.1047(9) Uani 1 1 d . . . . .
C47 C 1.39483(18) 0.29903(18) 0.15532(8) 0.0619(5) Uani 1 1 d . . . . .
H47 H 1.3879 0.3408 0.1843 0.074 Uiso 1 1 calc R U . . .
C51 C 1.32266(18) 0.16839(19) 0.09447(8) 0.0624(5) Uani 1 1 d . . . . .
H51 H 1.2666 0.1207 0.0822 0.075 Uiso 1 1 calc R U . . .
C3 C 0.64156(19) -0.4963(2) 0.03812(15) 0.0901(9) Uani 1 1 d . . . . .
H3 H 0.5869 -0.5501 0.0330 0.108 Uiso 1 1 calc R U . . .
C35 C 0.95937(17) 0.13808(19) 0.26469(8) 0.0624(5) Uani 1 1 d . . . . .
C44 C 1.17587(19) 0.41245(17) 0.17417(10) 0.0656(5) Uani 1 1 d . U . . .
H44 H 1.1984 0.4201 0.1417 0.079 Uiso 1 1 calc R U . . .
C30 C 0.9338(2) -0.1933(2) 0.21036(10) 0.0806(7) Uani 1 1 d . . . . .
H30 H 0.8605 -0.2168 0.2097 0.097 Uiso 1 1 calc R U . . .
C5 C 0.75260(18) -0.38026(19) 0.09382(10) 0.0687(6) Uani 1 1 d . . . . .
H5 H 0.7716 -0.3554 0.1264 0.082 Uiso 1 1 calc R U . . .
C20 C 1.27736(17) -0.15777(19) 0.04528(9) 0.0641(5) Uani 1 1 d . . . . .
H20 H 1.2459 -0.1015 0.0251 0.077 Uiso 1 1 calc R U . . .
C29 C 1.0181(3) -0.2705(2) 0.21168(10) 0.0867(8) Uani 1 1 d . . . . .
H29 H 1.0015 -0.3457 0.2114 0.104 Uiso 1 1 calc R U . . .
C1 C 0.77725(19) -0.3764(2) 0.00607(10) 0.0740(6) Uani 1 1 d . . . . .
H1 H 0.8128 -0.3488 -0.0211 0.089 Uiso 1 1 calc R U . . .
C28 C 1.1260(2) -0.23662(18) 0.21341(9) 0.0736(6) Uani 1 1 d . . . . .
H28 H 1.1829 -0.2886 0.2148 0.088 Uiso 1 1 calc R U . . .
N2 N 0.8952(2) 0.1258(3) 0.29105(10) 0.1150(10) Uani 1 1 d . . . . .
C38 C 0.91850(19) 0.41381(19) 0.21941(10) 0.0709(6) Uani 1 1 d . . . . .
H38 H 0.9015 0.3971 0.1856 0.085 Uiso 1 1 calc R U . . .
C23 C 1.3722(2) -0.3250(2) 0.10430(12) 0.0844(8) Uani 1 1 d . . . . .
H23 H 1.4047 -0.3817 0.1239 0.101 Uiso 1 1 calc R U . . .
C21 C 1.3902(2) -0.1760(3) 0.04721(13) 0.0884(8) Uani 1 1 d . . . . .
H21 H 1.4345 -0.1316 0.0285 0.106 Uiso 1 1 calc R U . . .
C48 C 1.4902(2) 0.3070(2) 0.13003(10) 0.0790(7) Uani 1 1 d . . . . .
H48 H 1.5473 0.3535 0.1423 0.095 Uiso 1 1 calc R U . . .
C42 C 1.0296(2) 0.3858(2) 0.29589(9) 0.0743(6) Uani 1 1 d . . . . .
H42 H 1.0872 0.3497 0.3143 0.089 Uiso 1 1 calc R U . . .
C50 C 1.4176(2) 0.1776(2) 0.06925(9) 0.0771(7) Uani 1 1 d . . . . .
H50 H 1.4248 0.1367 0.0401 0.093 Uiso 1 1 calc R U . . .
C4 C 0.6699(2) -0.4583(2) 0.08516(13) 0.0883(8) Uani 1 1 d . . . . .
H4 H 0.6331 -0.4851 0.1121 0.106 Uiso 1 1 calc R U . . .
C39 C 0.8565(2) 0.4918(2) 0.24273(14) 0.0897(8) Uani 1 1 d . . . . .
H39 H 0.7975 0.5265 0.2247 0.108 Uiso 1 1 calc R U . . .
C40 C 0.8809(3) 0.5177(2) 0.29145(15) 0.0994(11) Uani 1 1 d . . . . .
H40 H 0.8392 0.5710 0.3068 0.119 Uiso 1 1 calc R U . . .
C2 C 0.6936(2) -0.4555(2) -0.00183(13) 0.0935(9) Uani 1 1 d . . . . .
H2 H 0.6732 -0.4805 -0.0343 0.112 Uiso 1 1 calc R U . . .
C49 C 1.5014(2) 0.2470(2) 0.08707(10) 0.0801(7) Uani 1 1 d . . . . .
H49 H 1.5655 0.2532 0.0701 0.096 Uiso 1 1 calc R U . . .
C22 C 1.4371(2) -0.2589(3) 0.07648(14) 0.0959(10) Uani 1 1 d . . . . .
H22 H 1.5132 -0.2706 0.0776 0.115 Uiso 1 1 calc R U . . .
C41 C 0.9672(3) 0.4659(3) 0.31875(12) 0.1013(10) Uani 1 1 d . . . . .
H41 H 0.9838 0.4843 0.3524 0.122 Uiso 1 1 calc R U . . .
O2 O 1.17132(19) 0.49450(14) 0.19599(9) 0.0996(6) Uani 1 1 d . U . . .
O1 O 1.00866(19) -0.48072(14) 0.06981(10) 0.1097(7) 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 0.0181 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'
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
C12 C11 C16 118.27(16) . . ?
C12 C11 C10 121.81(15) . . ?
C16 C11 C10 119.88(15) . . ?
C7 C8 C10 121.51(15) . . ?
C7 C8 C9 118.43(14) . . ?
C10 C8 C9 119.96(15) . . ?
C10 C17 C18 123.37(14) . . ?
C45 C52 C33 123.20(16) . . ?
C17 C10 C8 117.02(15) . . ?
C17 C10 C11 119.76(14) . . ?
C8 C10 C11 123.22(15) . . ?
C15 C16 C11 120.83(18) . . ?
C7 C25 C18 120.22(15) . . ?
C7 C25 C26 120.39(15) . . ?
C18 C25 C26 119.22(15) . . ?
C17 C18 C25 118.52(15) . . ?
C17 C18 C19 118.78(14) . . ?
C25 C18 C19 122.69(15) . . ?
C1 C6 C5 119.29(18) . . ?
C1 C6 C7 120.57(18) . . ?
C5 C6 C7 120.13(17) . . ?
C36 C43 C45 120.08(16) . . ?
C36 C43 C44 121.23(17) . . ?
C45 C43 C44 118.63(17) . . ?
C36 C34 C33 121.99(16) . . ?
C36 C34 C35 117.59(17) . . ?
C33 C34 C35 120.41(17) . . ?
C52 C45 C43 118.78(16) . . ?
C52 C45 C46 117.80(16) . . ?
C43 C45 C46 123.34(16) . . ?
C52 C33 C34 116.91(15) . . ?
C52 C33 C32 118.60(16) . . ?
C34 C33 C32 124.48(16) . . ?
C30 C31 C32 120.0(2) . . ?
C25 C7 C8 119.27(14) . . ?
C25 C7 C6 121.57(15) . . ?
C8 C7 C6 119.09(15) . . ?
N1 C9 C8 172.8(3) . . ?
C51 C46 C47 118.02(18) . . ?
C51 C46 C45 120.53(17) . . ?
C47 C46 C45 121.12(17) . . ?
C34 C36 C43 118.85(16) . . ?
C34 C36 C37 118.73(16) . . ?
C43 C36 C37 122.41(16) . . ?
C13 C12 C11 120.49(18) . . ?
C31 C32 C27 118.19(18) . . ?
C31 C32 C33 122.19(18) . . ?
C27 C32 C33 119.46(17) . . ?
O1 C26 C25 133.0(2) . . ?
C14 C13 C12 120.5(2) . . ?
C28 C27 C32 121.3(2) . . ?
C42 C37 C38 119.2(2) . . ?
C42 C37 C36 120.49(19) . . ?
C38 C37 C36 120.25(18) . . ?
C19 C24 C23 119.4(2) . . ?
C14 C15 C16 120.32(19) . . ?
C15 C14 C13 119.54(19) . . ?
C24 C19 C20 119.25(18) . . ?
C24 C19 C18 122.11(17) . . ?
C20 C19 C18 118.62(17) . . ?
C48 C47 C46 120.5(2) . . ?
C50 C51 C46 121.1(2) . . ?
C4 C3 C2 119.8(2) . . ?
N2 C35 C34 176.8(3) . . ?
O2 C44 C43 131.5(2) . . ?
C29 C30 C31 120.6(2) . . ?
C6 C5 C4 119.9(2) . . ?
C21 C20 C19 120.2(2) . . ?
C28 C29 C30 120.1(2) . . ?
C6 C1 C2 119.9(2) . . ?
C29 C28 C27 119.8(2) . . ?
C37 C38 C39 120.6(3) . . ?
C22 C23 C24 120.6(3) . . ?
C22 C21 C20 120.4(3) . . ?
C49 C48 C47 120.5(2) . . ?
C37 C42 C41 119.5(3) . . ?
C49 C50 C51 120.2(2) . . ?
C3 C4 C5 121.0(3) . . ?
C40 C39 C38 120.4(3) . . ?
C39 C40 C41 120.3(2) . . ?
C3 C2 C1 120.0(3) . . ?
C48 C49 C50 119.7(2) . . ?
C21 C22 C23 120.2(2) . . ?
C40 C41 C42 120.0(3) . . ?
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
C11 C12 1.387(2) . ?
C11 C16 1.393(2) . ?
C11 C10 1.483(2) . ?
C8 C7 1.404(2) . ?
C8 C10 1.413(2) . ?
C8 C9 1.449(2) . ?
C17 C10 1.387(2) . ?
C17 C18 1.389(2) . ?
C52 C45 1.386(2) . ?
C52 C33 1.390(2) . ?
C16 C15 1.378(3) . ?
C25 C7 1.399(2) . ?
C25 C18 1.409(2) . ?
C25 C26 1.485(3) . ?
C18 C19 1.483(2) . ?
C6 C1 1.375(3) . ?
C6 C5 1.380(3) . ?
C6 C7 1.495(2) . ?
C43 C36 1.404(2) . ?
C43 C45 1.408(2) . ?
C43 C44 1.486(3) . ?
C34 C36 1.403(2) . ?
C34 C33 1.406(2) . ?
C34 C35 1.453(3) . ?
C45 C46 1.488(2) . ?
C33 C32 1.484(2) . ?
C31 C30 1.386(3) . ?
C31 C32 1.392(3) . ?
C9 N1 1.088(3) . ?
C46 C51 1.386(3) . ?
C46 C47 1.389(3) . ?
C36 C37 1.498(2) . ?
C12 C13 1.382(3) . ?
C32 C27 1.396(3) . ?
C26 O1 1.128(3) . ?
C13 C14 1.378(3) . ?
C27 C28 1.381(3) . ?
C37 C42 1.377(3) . ?
C37 C38 1.379(3) . ?
C24 C19 1.389(3) . ?
C24 C23 1.393(3) . ?
C15 C14 1.373(3) . ?
C19 C20 1.399(3) . ?
C47 C48 1.383(3) . ?
C51 C50 1.378(3) . ?
C3 C4 1.353(4) . ?
C3 C2 1.368(4) . ?
C35 N2 1.095(3) . ?
C44 O2 1.152(3) . ?
C30 C29 1.381(4) . ?
C5 C4 1.381(3) . ?
C20 C21 1.380(3) . ?
C29 C28 1.366(4) . ?
C1 C2 1.396(3) . ?
C38 C39 1.380(3) . ?
C23 C22 1.375(4) . ?
C21 C22 1.365(4) . ?
C48 C49 1.369(4) . ?
C42 C41 1.395(4) . ?
C50 C49 1.372(4) . ?
C39 C40 1.345(5) . ?
C40 C41 1.377(5) . ?
