#------------------------------------------------------------------------------
#$Date: 2021-09-03 23:25:08 +0300 (Fri, 03 Sep 2021) $
#$Revision: 268433 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519008.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_4519008
loop_
_publ_author_name
'Mukhopadhyay, Arindam'
'Jindal, Swati'
'Maka, Vijay Kumar'
'Moorthy, Jarugu Narasimha'
_publ_section_title
;
 Contrasting Photochromic and Acidochromic Behaviors of Pyridyl- and
 Pyrimidylethynylated Mono- and Bis-Benzopyrans.
;
_journal_issue                   32
_journal_name_full               'ACS omega'
_journal_page_first              21113
_journal_page_last               21124
_journal_paper_doi               10.1021/acsomega.1c02948
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C50 H32 N2 O2, 2(C H Cl3)'
_chemical_formula_sum            'C52 H34 Cl6 N2 O2'
_chemical_formula_weight         931.51
_chemical_name_common            Py-BBP
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/5
_cell_angle_alpha                108.353(2)
_cell_angle_beta                 100.322(2)
_cell_angle_gamma                94.923(2)
_cell_formula_units_Z            1
_cell_length_a                   8.6204(5)
_cell_length_b                   9.5160(5)
_cell_length_c                   14.2523(9)
_cell_measurement_reflns_used    3993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.334
_cell_measurement_theta_min      2.282
_cell_volume                     1078.97(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9433
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         2.282
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboidal
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.070
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0447
_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)+(0.0323P)²+0.9530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3993
_reflns_number_total             5303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c02948_si_002.cif
_cod_data_source_block           Py-BBP
_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/current/ACS/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 
;
_cod_database_code               4519008
_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.
;
_shelxl_version_number           2014/5
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 0.74083(7) 0.78138(6) 0.39632(4) 0.02262(14) Uani 1 1 d . . . . .
Cl2 Cl 0.96941(8) 0.68720(8) 0.52916(5) 0.03447(17) Uani 1 1 d . . . . .
Cl3 Cl 0.88438(7) 0.98341(7) 0.59877(4) 0.02989(16) Uani 1 1 d . . . . .
C26 C 0.8155(3) 0.7953(2) 0.52294(16) 0.0188(4) Uani 1 1 d . . . . .
H26 H 0.7290 0.7566 0.5485 0.023 Uiso 1 1 calc R U . . .
O1 O 0.34852(15) 0.19209(14) 0.12883(10) 0.0102(3) Uani 1 1 d . . . . .
N1 N -0.3496(2) -0.2718(3) 0.12956(18) 0.0333(5) Uani 1 1 d . . . . .
C1 C -0.2688(3) -0.1330(3) 0.17420(19) 0.0294(6) Uani 1 1 d . . . . .
H1 H -0.3086 -0.0663 0.2239 0.035 Uiso 1 1 calc R U . . .
C2 C -0.1296(3) -0.0820(3) 0.15130(16) 0.0193(5) Uani 1 1 d . . . . .
H2 H -0.0785 0.0160 0.1847 0.023 Uiso 1 1 calc R U . . .
C3 C -0.0679(2) -0.1807(2) 0.07720(15) 0.0127(4) Uani 1 1 d . . . . .
C4 C -0.1515(2) -0.3254(2) 0.02889(16) 0.0179(4) Uani 1 1 d . . . . .
H4 H -0.1150 -0.3945 -0.0214 0.022 Uiso 1 1 calc R U . . .
C5 C -0.2902(3) -0.3639(3) 0.05731(19) 0.0267(6) Uani 1 1 d . . . . .
H5 H -0.3457 -0.4603 0.0239 0.032 Uiso 1 1 calc R U . . .
C6 C 0.0773(2) -0.1348(2) 0.05210(14) 0.0113(4) Uani 1 1 d . . . . .
C7 C 0.2004(2) -0.0961(2) 0.03396(14) 0.0103(4) Uani 1 1 d . . . . .
C8 C 0.3505(2) -0.0483(2) 0.01537(14) 0.0089(4) Uani 1 1 d . . . . .
C9 C 0.4291(2) 0.0977(2) 0.06815(14) 0.0088(4) Uani 1 1 d . . . . .
C10 C 0.5780(2) 0.1474(2) 0.05471(14) 0.0092(4) Uani 1 1 d . . . . .
C11 C 0.6499(2) 0.3007(2) 0.11265(14) 0.0115(4) Uani 1 1 d . . . . .
H11 H 0.7421 0.3413 0.0993 0.014 Uiso 1 1 calc R U . . .
C12 C 0.5849(2) 0.3837(2) 0.18494(14) 0.0116(4) Uani 1 1 d . . . . .
H12 H 0.6310 0.4828 0.2198 0.014 Uiso 1 1 calc R U . . .
C13 C 0.4385(2) 0.3219(2) 0.21210(14) 0.0095(4) Uani 1 1 d . . . . .
C14 C 0.4911(2) 0.2748(2) 0.30458(14) 0.0110(4) Uani 1 1 d . . . . .
C15 C 0.4595(2) 0.1279(2) 0.30154(15) 0.0149(4) Uani 1 1 d . . . . .
H15 H 0.3998 0.0552 0.2427 0.018 Uiso 1 1 calc R U . . .
C16 C 0.5168(3) 0.0885(3) 0.38609(17) 0.0205(5) Uani 1 1 d . . . . .
H16 H 0.4961 -0.0105 0.3832 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6042(3) 0.1955(3) 0.47421(17) 0.0221(5) Uani 1 1 d . . . . .
H17 H 0.6433 0.1686 0.5303 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6331(3) 0.3427(3) 0.47868(16) 0.0221(5) Uani 1 1 d . . . . .
H18 H 0.6900 0.4154 0.5384 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5777(2) 0.3824(2) 0.39466(15) 0.0170(4) Uani 1 1 d . . . . .
H19 H 0.5984 0.4817 0.3982 0.020 Uiso 1 1 calc R U . . .
C20 C 0.3168(2) 0.4301(2) 0.22960(14) 0.0099(4) Uani 1 1 d . . . . .
C21 C 0.1759(2) 0.3823(2) 0.25366(14) 0.0123(4) Uani 1 1 d . . . . .
H21 H 0.1608 0.2889 0.2613 0.015 Uiso 1 1 calc R U . . .
C22 C 0.0586(2) 0.4730(2) 0.26620(15) 0.0157(4) Uani 1 1 d . . . . .
H22 H -0.0347 0.4404 0.2824 0.019 Uiso 1 1 calc R U . . .
C23 C 0.0798(3) 0.6121(2) 0.25462(16) 0.0180(4) Uani 1 1 d . . . . .
H23 H 0.0008 0.6729 0.2629 0.022 Uiso 1 1 calc R U . . .
C24 C 0.2193(2) 0.6603(2) 0.23068(15) 0.0172(4) Uani 1 1 d . . . . .
H24 H 0.2336 0.7535 0.2228 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3377(2) 0.5699(2) 0.21842(14) 0.0130(4) Uani 1 1 d . . . . .
H25 H 0.4311 0.6031 0.2027 0.016 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'
O O 0.0106 0.0060 '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'
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
Cl2 C26 Cl3 110.42(12) . . ?
Cl2 C26 Cl1 110.07(12) . . ?
Cl3 C26 Cl1 110.50(12) . . ?
Cl2 C26 H26 108.6 . . ?
Cl3 C26 H26 108.6 . . ?
Cl1 C26 H26 108.6 . . ?
C9 O1 C13 119.04(14) . . ?
C1 N1 C5 116.1(2) . . ?
N1 C1 C2 124.4(2) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 117.90(19) . . ?
C4 C3 C6 121.22(19) . . ?
C2 C3 C6 120.88(19) . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 124.4(2) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C7 C6 C3 178.1(2) . . ?
C6 C7 C8 178.3(2) . . ?
C9 C8 C10 119.26(16) . 2_655 ?
C9 C8 C7 119.82(17) . . ?
C10 C8 C7 120.91(17) 2_655 . ?
O1 C9 C10 121.59(16) . . ?
O1 C9 C8 116.60(16) . . ?
C10 C9 C8 121.68(17) . . ?
C9 C10 C8 119.04(17) . 2_655 ?
C9 C10 C11 117.67(17) . . ?
C8 C10 C11 123.27(17) 2_655 . ?
C12 C11 C10 120.33(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 122.03(17) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
O1 C13 C12 111.04(15) . . ?
O1 C13 C14 108.89(15) . . ?
C12 C13 C14 108.71(15) . . ?
O1 C13 C20 103.09(14) . . ?
C12 C13 C20 113.53(16) . . ?
C14 C13 C20 111.43(15) . . ?
C15 C14 C19 118.66(18) . . ?
C15 C14 C13 122.25(17) . . ?
C19 C14 C13 119.06(17) . . ?
C14 C15 C16 120.35(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C25 C20 C21 119.13(18) . . ?
C25 C20 C13 122.93(17) . . ?
C21 C20 C13 117.88(17) . . ?
C22 C21 C20 120.47(19) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.15(19) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 119.71(19) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.35(19) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C20 C25 C24 120.19(19) . . ?
C20 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
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 C26 1.763(2) . ?
Cl2 C26 1.754(2) . ?
Cl3 C26 1.759(2) . ?
C26 H26 0.9800 . ?
O1 C9 1.368(2) . ?
O1 C13 1.455(2) . ?
N1 C1 1.337(3) . ?
N1 C5 1.338(3) . ?
C1 C2 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 C6 1.432(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.192(3) . ?
C7 C8 1.432(3) . ?
C8 C9 1.397(3) . ?
C8 C10 1.412(3) 2_655 ?
C9 C10 1.396(3) . ?
C10 C8 1.412(3) 2_655 ?
C10 C11 1.448(3) . ?
C11 C12 1.331(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.510(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.528(3) . ?
C13 C20 1.530(3) . ?
C14 C15 1.387(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.389(3) . ?
C20 C21 1.397(3) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
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
C5 N1 C1 C2 -1.0(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 C6 -178.7(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C6 C3 C4 C5 179.16(19) . . . . ?
C1 N1 C5 C4 1.6(3) . . . . ?
C3 C4 C5 N1 -0.8(3) . . . . ?
C13 O1 C9 C10 -26.6(2) . . . . ?
C13 O1 C9 C8 157.38(16) . . . . ?
C10 C8 C9 O1 174.91(16) 2_655 . . . ?
C7 C8 C9 O1 -6.0(3) . . . . ?
C10 C8 C9 C10 -1.1(3) 2_655 . . . ?
C7 C8 C9 C10 177.95(17) . . . . ?
O1 C9 C10 C8 -174.72(16) . . . 2_655 ?
C8 C9 C10 C8 1.1(3) . . . 2_655 ?
O1 C9 C10 C11 4.1(3) . . . . ?
C8 C9 C10 C11 179.89(17) . . . . ?
C9 C10 C11 C12 8.2(3) . . . . ?
C8 C10 C11 C12 -173.04(19) 2_655 . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C9 O1 C13 C12 33.8(2) . . . . ?
C9 O1 C13 C14 -85.83(18) . . . . ?
C9 O1 C13 C20 155.74(15) . . . . ?
C11 C12 C13 O1 -22.1(3) . . . . ?
C11 C12 C13 C14 97.7(2) . . . . ?
C11 C12 C13 C20 -137.73(19) . . . . ?
O1 C13 C14 C15 2.7(2) . . . . ?
C12 C13 C14 C15 -118.40(19) . . . . ?
C20 C13 C14 C15 115.8(2) . . . . ?
O1 C13 C14 C19 -179.01(16) . . . . ?
C12 C13 C14 C19 59.9(2) . . . . ?
C20 C13 C14 C19 -66.0(2) . . . . ?
C19 C14 C15 C16 -1.6(3) . . . . ?
C13 C14 C15 C16 176.69(18) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C15 C14 C19 C18 1.0(3) . . . . ?
C13 C14 C19 C18 -177.32(19) . . . . ?
O1 C13 C20 C25 -118.37(18) . . . . ?
C12 C13 C20 C25 1.8(3) . . . . ?
C14 C13 C20 C25 124.99(19) . . . . ?
O1 C13 C20 C21 58.8(2) . . . . ?
C12 C13 C20 C21 179.06(16) . . . . ?
C14 C13 C20 C21 -57.8(2) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
C13 C20 C21 C22 -177.32(17) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C21 C20 C25 C24 -0.3(3) . . . . ?
C13 C20 C25 C24 176.91(17) . . . . ?
C23 C24 C25 C20 0.3(3) . . . . ?
