#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:23:30 +0300 (Sun, 06 Sep 2020) $
#$Revision: 255980 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/70/7127054.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_7127054
loop_
_publ_author_name
'Wang, Ding'
'Ma, Zhishuang'
'Wang, Nana'
'Li, Chenyu'
'Wang, Tao'
'Liang, Yong'
'Zhang, Zunting'
_publ_section_title
;
 Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin via a TsOH-mediated
 tandem reaction.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10369
_journal_page_last               10372
_journal_paper_doi               10.1039/d0cc04452k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C27 H19 N O3'
_chemical_formula_sum            'C27 H19 N O3'
_chemical_formula_weight         405.44
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-05-25 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.73920(10)
_cell_length_b                   11.05470(10)
_cell_length_c                   19.1794(2)
_cell_measurement_reflns_used    12815
_cell_measurement_temperature    180
_cell_measurement_theta_max      75.5890
_cell_measurement_theta_min      2.3820
_cell_volume                     2020.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16576
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.753
_diffrn_reflns_theta_min         6.186
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       transparent
_exptl_crystal_F_000             773
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0631P)²+0.6596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3748
_reflns_number_total             4027
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04452k2.cif
_cod_data_source_block           3
_cod_depositor_comments          'Adding full bibliography for 7127054.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7127054
_shelx_shelxl_version_number     2014/7
_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.
;
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
O001 O 0.59409(11) 0.06871(8) 0.60105(6) 0.0434(3) Uani 1 1 d . . . . .
O002 O 0.48718(11) 0.47475(8) 0.65471(5) 0.0426(3) Uani 1 1 d . . . . .
O003 O 0.44579(11) 0.65641(9) 0.68905(5) 0.0451(3) Uani 1 1 d . . . . .
N004 N 0.18287(14) 1.14249(11) 0.80824(7) 0.0458(3) Uani 1 1 d . . . . .
C00A C 0.19990(14) 1.06708(12) 0.77022(7) 0.0354(3) Uani 1 1 d . . . . .
C00B C 0.18814(14) 0.50877(11) 0.46398(7) 0.0317(3) Uani 1 1 d . . . . .
H00B H 0.1794 0.4486 0.4294 0.038 Uiso 1 1 calc R U . . .
C00C C 0.21174(13) 0.97083(11) 0.72111(7) 0.0313(3) Uani 1 1 d . . . . .
C00D C 0.09386(13) 0.60656(12) 0.45366(7) 0.0315(3) Uani 1 1 d . . . . .
C00E C 0.30995(14) 0.88838(12) 0.62667(7) 0.0341(3) Uani 1 1 d . . . . .
H00E H 0.3719 0.8942 0.5958 0.041 Uiso 1 1 calc R U . . .
C00F C 0.45080(14) 0.18819(12) 0.51467(7) 0.0347(3) Uani 1 1 d . . . . .
H00F H 0.4455 0.1234 0.4833 0.042 Uiso 1 1 calc R U . . .
C00G C 0.10784(13) 0.69980(11) 0.50577(7) 0.0316(3) Uani 1 1 d . . . . .
C00H C 0.30625(14) 0.97898(12) 0.67582(7) 0.0343(3) Uani 1 1 d . . . . .
H00H H 0.3664 1.0449 0.6786 0.041 Uiso 1 1 calc R U . . .
C00I C 0.12858(15) 0.78101(12) 0.66859(8) 0.0373(3) Uani 1 1 d . . . . .
H00I H 0.0691 0.7146 0.6661 0.045 Uiso 1 1 calc R U . . .
C00J C 0.21718(13) 0.69226(11) 0.56764(7) 0.0299(3) Uani 1 1 d . . . . .
C00K C 0.37716(14) 0.29273(12) 0.49327(7) 0.0337(3) Uani 1 1 d . . . . .
H00K H 0.3226 0.2973 0.4475 0.040 Uiso 1 1 calc R U . . .
C00L C 0.41608(14) 0.58198(11) 0.64295(7) 0.0334(3) Uani 1 1 d . . . . .
C00M C 0.12333(15) 0.87153(12) 0.71785(7) 0.0370(3) Uani 1 1 d . . . . .
H00M H 0.0611 0.8659 0.7485 0.044 Uiso 1 1 calc R U . . .
C00N C 0.47037(14) 0.38163(11) 0.60544(7) 0.0335(3) Uani 1 1 d . . . . .
C00O C 0.00841(15) 0.79627(13) 0.49455(8) 0.0385(3) Uani 1 1 d . . . . .
H00O H 0.0163 0.8586 0.5277 0.046 Uiso 1 1 calc R U . . .
C00P C -0.11197(15) 0.70593(14) 0.38462(8) 0.0419(3) Uani 1 1 d . . . . .
H00P H -0.1848 0.7088 0.3448 0.050 Uiso 1 1 calc R U . . .
C00Q C 0.54559(15) 0.27738(12) 0.62926(8) 0.0390(3) Uani 1 1 d . . . . .
H00Q H 0.6022 0.2738 0.6746 0.047 Uiso 1 1 calc R U . . .
C00R C -0.01885(14) 0.61184(13) 0.39309(7) 0.0370(3) Uani 1 1 d . . . . .
H00R H -0.0291 0.5508 0.3591 0.044 Uiso 1 1 calc R U . . .
C00S C -0.09786(15) 0.79842(14) 0.43599(8) 0.0429(3) Uani 1 1 d . . . . .
H00S H -0.1619 0.8619 0.4299 0.052 Uiso 1 1 calc R U . . .
C00T C 0.69769(15) 0.05617(12) 0.66732(8) 0.0395(3) Uani 1 1 d . . . . .
H00T H 0.6651 0.0988 0.7057 0.047 Uiso 1 1 calc R U . . .
C00U C 0.83391(17) 0.10923(16) 0.65774(11) 0.0550(4) Uani 1 1 d . . . . .
H00A H 0.8684 0.0642 0.6221 0.082 Uiso 1 1 calc R U . . .
H00C H 0.9010 0.1055 0.7020 0.082 Uiso 1 1 calc R U . . .
H00D H 0.8198 0.1920 0.6429 0.082 Uiso 1 1 calc R U . . .
C00V C 0.70786(19) -0.07726(15) 0.68335(11) 0.0584(5) Uani 1 1 d . . . . .
H00G H 0.6180 -0.1069 0.6887 0.088 Uiso 1 1 calc R U . . .
H00J H 0.7756 -0.0907 0.7267 0.088 Uiso 1 1 calc R U . . .
H00L H 0.7365 -0.1192 0.6449 0.088 Uiso 1 1 calc R U . . .
C005 C 0.29331(13) 0.49984(11) 0.52411(6) 0.0288(3) Uani 1 1 d . . . . .
C006 C 0.22188(13) 0.78851(11) 0.62288(7) 0.0305(3) Uani 1 1 d . . . . .
C007 C 0.30788(13) 0.59349(11) 0.57652(6) 0.0293(3) Uani 1 1 d . . . . .
C008 C 0.53376(14) 0.17899(11) 0.58353(7) 0.0349(3) Uani 1 1 d . . . . .
C009 C 0.38253(13) 0.39267(11) 0.53907(7) 0.0300(3) 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'
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'
H H 0.0000 0.0000 '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
C008 O001 C00T 119.03(10) . . ?
C00L O002 C00N 123.18(10) . . ?
N004 C00A C00C 176.32(15) . . ?
C005 C00B C00D 121.59(12) . . ?
C00M C00C C00H 120.43(12) . . ?
C00M C00C C00A 118.73(12) . . ?
C00H C00C C00A 120.79(12) . . ?
C00B C00D C00G 119.54(12) . . ?
C00B C00D C00R 121.15(12) . . ?
C00G C00D C00R 119.28(12) . . ?
C00H C00E C006 120.60(12) . . ?
C00K C00F C008 120.33(12) . . ?
C00D C00G C00J 119.34(11) . . ?
C00D C00G C00O 118.15(12) . . ?
C00J C00G C00O 122.49(12) . . ?
C00E C00H C00C 119.49(12) . . ?
C00M C00I C006 120.56(12) . . ?
C007 C00J C00G 119.63(11) . . ?
C007 C00J C006 123.02(11) . . ?
C00G C00J C006 117.21(11) . . ?
C00F C00K C009 121.54(12) . . ?
O003 C00L O002 115.85(12) . . ?
O003 C00L C007 126.58(12) . . ?
O002 C00L C007 117.53(11) . . ?
C00I C00M C00C 119.51(12) . . ?
O002 C00N C009 121.72(11) . . ?
O002 C00N C00Q 114.31(11) . . ?
C009 C00N C00Q 123.95(12) . . ?
C00S C00O C00G 120.96(13) . . ?
C00R C00P C00S 120.18(13) . . ?
C008 C00Q C00N 118.18(12) . . ?
C00P C00R C00D 120.56(13) . . ?
C00O C00S C00P 120.86(13) . . ?
O001 C00T C00U 109.13(13) . . ?
O001 C00T C00V 106.01(12) . . ?
C00U C00T C00V 112.73(13) . . ?
C00B C005 C007 119.03(11) . . ?
C00B C005 C009 122.07(11) . . ?
C007 C005 C009 118.67(11) . . ?
C00I C006 C00E 119.40(12) . . ?
C00I C006 C00J 118.42(11) . . ?
C00E C006 C00J 122.04(11) . . ?
C00J C007 C005 120.87(11) . . ?
C00J C007 C00L 119.55(11) . . ?
C005 C007 C00L 119.49(11) . . ?
O001 C008 C00Q 124.69(12) . . ?
O001 C008 C00F 115.58(11) . . ?
C00Q C008 C00F 119.68(12) . . ?
C00N C009 C00K 116.20(11) . . ?
C00N C009 C005 118.77(11) . . ?
C00K C009 C005 124.75(12) . . ?
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
O001 C008 1.3649(15) . ?
O001 C00T 1.4578(17) . ?
O002 C00L 1.3679(15) . ?
O002 C00N 1.3840(15) . ?
O003 C00L 1.1988(16) . ?
N004 C00A 1.1419(18) . ?
C00A C00C 1.4413(18) . ?
C00B C005 1.3794(18) . ?
C00B C00D 1.4058(18) . ?
C00C C00M 1.3885(19) . ?
C00C C00H 1.3925(18) . ?
C00D C00G 1.4226(18) . ?
C00D C00R 1.4258(18) . ?
C00E C00H 1.3809(18) . ?
C00E C006 1.3907(18) . ?
C00F C00K 1.3773(18) . ?
C00F C008 1.4029(19) . ?
C00G C00J 1.4244(18) . ?
C00G C00O 1.4267(18) . ?
C00I C00M 1.3844(19) . ?
C00I C006 1.3889(18) . ?
C00J C007 1.3927(17) . ?
C00J C006 1.4955(17) . ?
C00K C009 1.4057(18) . ?
C00L C007 1.4823(18) . ?
C00N C009 1.3853(18) . ?
C00N C00Q 1.3914(18) . ?
C00O C00S 1.362(2) . ?
C00P C00R 1.368(2) . ?
C00P C00S 1.407(2) . ?
C00Q C008 1.3871(19) . ?
C00T C00U 1.496(2) . ?
C00T C00V 1.506(2) . ?
C005 C007 1.4296(17) . ?
C005 C009 1.4623(17) . ?
