#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:21:51 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240737.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_7240737
loop_
_publ_author_name
'Akhtar, Muhammad Saeed'
'Thombal, Raju S.'
'Inductivo Tamargo, Ramuel John'
'Yang, Won-Guen'
'Kim, Sung Hong'
'Lee, Yong Rok'
_publ_section_title
;
 Eco-friendly organocatalyst- and reagent-controlled selective
 construction of diverse and multifunctionalized 2-hydroxybenzophenone
 frameworks for potent UV-A/B filters by cascade benzannulation
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              4523
_journal_page_last               4531
_journal_paper_doi               10.1039/D0GC01011A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 O3'
_chemical_formula_sum            'C19 H14 O3'
_chemical_formula_weight         290.30
_chemical_melting_point          445
_chemical_name_systematic        3-(2-hydroxy-5-methylbenzoyl)-1-naphthaldehyde
_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
;
2020-03-21 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2808(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3618(3)
_cell_length_b                   7.4104(2)
_cell_length_c                   25.4612(9)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.86
_cell_volume                     1383.11(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'PHOTON II M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42946
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.591
_diffrn_reflns_theta_min         2.864
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/ethyl acetate'
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0429
_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)+(0.0452P)²+0.7069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2986
_reflns_number_total             3455
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc01011a2.cif
_cod_data_source_block           MS422
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7240736--7240737.cif.

 Adding full bibliography for 7240736--7240737.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240737
_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. 
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.985
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
C1 C 0.54885(18) 0.65219(18) 0.82189(5) 0.0277(3) Uani 1 1 d . . . . .
C2 C 0.42381(17) 0.53508(16) 0.84317(5) 0.0231(2) Uani 1 1 d . . . . .
C3 C 0.24993(17) 0.51379(16) 0.81645(5) 0.0237(2) Uani 1 1 d . . . . .
H3 H 0.1653 0.4380 0.8310 0.028 Uiso 1 1 calc R U . . .
C4 C 0.19890(18) 0.60118(17) 0.76915(5) 0.0268(3) Uani 1 1 d . . . . .
C5 C 0.3282(2) 0.71251(18) 0.74855(5) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.2974 0.7718 0.7163 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4998(2) 0.73784(19) 0.77421(5) 0.0321(3) Uani 1 1 d . . . . .
H6 H 0.5839 0.8134 0.7593 0.039 Uiso 1 1 calc R U . . .
O1 O 0.71840(14) 0.68513(17) 0.84573(4) 0.0418(3) Uani 1 1 d . . . . .
H1 H 0.7290 0.6369 0.8753 0.063 Uiso 1 1 calc R U . . .
C7 C 0.47246(17) 0.44822(17) 0.89484(5) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.58758(14) 0.51725(14) 0.92683(4) 0.0342(2) Uani 1 1 d . . . . .
C8 C 0.38561(17) 0.27432(17) 0.90823(5) 0.0237(2) Uani 1 1 d . . . . .
C9 C 0.35614(17) 0.24128(17) 0.96013(5) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.3835 0.3310 0.9857 0.029 Uiso 1 1 calc R U . . .
C10 C 0.28532(16) 0.07384(17) 0.97508(5) 0.0237(2) Uani 1 1 d . . . . .
C11 C 0.25183(17) 0.03739(18) 1.02803(5) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.2760 0.1267 1.0540 0.032 Uiso 1 1 calc R U . . .
C12 C 0.18454(17) -0.12673(19) 1.04175(5) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.14792(18) -0.26293(19) 1.00323(6) 0.0309(3) Uani 1 1 d . . . . .
H13 H 0.1025 -0.3753 1.0131 0.037 Uiso 1 1 calc R U . . .
C14 C 0.17807(19) -0.23212(18) 0.95196(5) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.1527 -0.3233 0.9267 0.036 Uiso 1 1 calc R U . . .
C15 C 0.24774(17) -0.06290(17) 0.93636(5) 0.0247(3) Uani 1 1 d . . . . .
C16 C 0.28132(18) -0.02588(17) 0.88358(5) 0.0273(3) Uani 1 1 d . . . . .
H16 H 0.2579 -0.1153 0.8577 0.033 Uiso 1 1 calc R U . . .
C17 C 0.34743(18) 0.13827(17) 0.86974(5) 0.0265(3) Uani 1 1 d . . . . .
H17 H 0.3677 0.1609 0.8344 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0133(2) 0.5749(2) 0.74037(6) 0.0387(3) Uani 1 1 d . . . . .
H18A H 0.0102 0.4612 0.7214 0.058 Uiso 1 1 calc R U . . .
H18B H -0.0123 0.6731 0.7156 0.058 Uiso 1 1 calc R U . . .
H18C H -0.0780 0.5735 0.7655 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1516(2) -0.1583(2) 1.09731(6) 0.0358(3) Uani 1 1 d . . . . .
H19 H 0.1747 -0.0624 1.1211 0.043 Uiso 1 1 calc R U . . .
O3 O 0.09693(17) -0.29870(17) 1.11449(5) 0.0476(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 0.0033 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'
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
O1 C1 C6 117.56(12) . . ?
O1 C1 C2 122.99(12) . . ?
C6 C1 C2 119.44(12) . . ?
C3 C2 C1 118.83(11) . . ?
C3 C2 C7 121.22(11) . . ?
C1 C2 C7 119.79(11) . . ?
C4 C3 C2 122.04(12) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 117.49(12) . . ?
C3 C4 C18 121.60(12) . . ?
C5 C4 C18 120.90(12) . . ?
C6 C5 C4 121.86(12) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.30(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C1 O1 H1 109.5 . . ?
O2 C7 C2 120.22(12) . . ?
O2 C7 C8 119.41(11) . . ?
C2 C7 C8 120.36(11) . . ?
C9 C8 C17 119.83(12) . . ?
C9 C8 C7 118.70(11) . . ?
C17 C8 C7 121.25(11) . . ?
C8 C9 C10 120.56(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 121.63(12) . . ?
C9 C10 C15 119.48(11) . . ?
C11 C10 C15 118.89(12) . . ?
C12 C11 C10 120.65(12) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.41(12) . . ?
C11 C12 C19 118.72(13) . . ?
C13 C12 C19 120.87(13) . . ?
C14 C13 C12 120.43(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.59(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C10 118.68(12) . . ?
C16 C15 C14 122.28(12) . . ?
C10 C15 C14 119.04(11) . . ?
C17 C16 C15 120.94(12) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C8 120.50(11) . . ?
C16 C17 H17 119.8 . . ?
C8 C17 H17 119.8 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 C12 124.88(15) . . ?
O3 C19 H19 117.6 . . ?
C12 C19 H19 117.6 . . ?
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
C1 O1 1.3588(17) . ?
C1 C6 1.3879(19) . ?
C1 C2 1.4093(17) . ?
C2 C3 1.4022(17) . ?
C2 C7 1.4786(16) . ?
C3 C4 1.3884(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3977(19) . ?
C4 C18 1.503(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
O1 H1 0.8300 . ?
C7 O2 1.2314(16) . ?
C7 C8 1.4920(18) . ?
C8 C9 1.3805(17) . ?
C8 C17 1.4159(17) . ?
C9 C10 1.4117(17) . ?
C9 H9 0.9400 . ?
C10 C11 1.4186(17) . ?
C10 C15 1.4231(17) . ?
C11 C12 1.3706(19) . ?
C11 H11 0.9400 . ?
C12 C13 1.416(2) . ?
C12 C19 1.4756(18) . ?
C13 C14 1.3634(19) . ?
C13 H13 0.9400 . ?
C14 C15 1.4252(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.4155(17) . ?
C16 C17 1.3683(18) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 O3 1.2113(19) . ?
C19 H19 0.9400 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.83 1.96 2.6657(15) 142.2 .
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
O1 C1 C2 C3 178.13(12) . . . . ?
C6 C1 C2 C3 -2.47(18) . . . . ?
O1 C1 C2 C7 2.72(19) . . . . ?
C6 C1 C2 C7 -177.89(12) . . . . ?
C1 C2 C3 C4 1.51(18) . . . . ?
C7 C2 C3 C4 176.86(11) . . . . ?
C2 C3 C4 C5 0.15(18) . . . . ?
C2 C3 C4 C18 178.94(12) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C18 C4 C5 C6 -179.68(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
O1 C1 C6 C5 -178.77(13) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C3 C2 C7 O2 -151.40(12) . . . . ?
C1 C2 C7 O2 23.90(18) . . . . ?
C3 C2 C7 C8 29.91(17) . . . . ?
C1 C2 C7 C8 -154.79(11) . . . . ?
O2 C7 C8 C9 33.64(17) . . . . ?
C2 C7 C8 C9 -147.66(12) . . . . ?
O2 C7 C8 C17 -141.09(13) . . . . ?
C2 C7 C8 C17 37.60(17) . . . . ?
C17 C8 C9 C10 -1.05(18) . . . . ?
C7 C8 C9 C10 -175.86(11) . . . . ?
C8 C9 C10 C11 -179.25(11) . . . . ?
C8 C9 C10 C15 1.30(18) . . . . ?
C9 C10 C11 C12 -179.41(11) . . . . ?
C15 C10 C11 C12 0.04(18) . . . . ?
C10 C11 C12 C13 0.22(19) . . . . ?
C10 C11 C12 C19 -179.90(12) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C19 C12 C13 C14 179.71(13) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C9 C10 C15 C16 -0.55(18) . . . . ?
C11 C10 C15 C16 179.98(11) . . . . ?
C9 C10 C15 C14 179.35(11) . . . . ?
C11 C10 C15 C14 -0.12(18) . . . . ?
C13 C14 C15 C16 179.83(12) . . . . ?
C13 C14 C15 C10 -0.07(19) . . . . ?
C10 C15 C16 C17 -0.43(19) . . . . ?
C14 C15 C16 C17 179.67(12) . . . . ?
C15 C16 C17 C8 0.69(19) . . . . ?
C9 C8 C17 C16 0.06(19) . . . . ?
C7 C8 C17 C16 174.73(12) . . . . ?
C11 C12 C19 O3 -178.06(14) . . . . ?
C13 C12 C19 O3 1.8(2) . . . . ?
