# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_865
_database_code_depnum_ccdc_archive 'CCDC 2051315'
loop_
_audit_author_name
_audit_author_address
'Mahsa Armaghan'
;HHU
Germany
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_publcif_datablock.id            {f05b1e70-af3c-44a0-aefc-f800570ff470}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3-phenyl-1H-pyrano[4,3-b]quinolin-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 N O2'
_chemical_formula_sum            'C18 H11 N O2'
_chemical_formula_weight         273.28

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1600(16)
_cell_length_b                   5.6000(11)
_cell_length_c                   27.700(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.00(3)
_cell_angle_gamma                90
_cell_volume                     1262.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7655
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      59.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  IPDS
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11016
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.559
_diffrn_reflns_theta_max         27.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2697
_reflns_number_gt                1989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2009)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'DIAMOND 4.2.2 (Crystal Impact, 2016)'
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0224P)²+1.1086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2697
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_restrained_S_all      1.331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.2628(3) 0.2175(4) 0.62922(8) 0.0415(6) Uani 1 1 d . . . . .
O2 O 0.0984(3) 0.0106(4) 0.57822(8) 0.0447(6) Uani 1 1 d . . . . .
N1 N 0.3625(3) 0.7090(4) 0.52549(9) 0.0362(6) Uani 1 1 d . . . . .
C1 C 0.4237(4) 0.4103(6) 0.69229(11) 0.0369(7) Uani 1 1 d . . . . .
C2 C 0.5337(4) 0.5823(6) 0.71076(12) 0.0464(8) Uani 1 1 d . . . . .
H2 H 0.568225 0.703062 0.690201 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5935(5) 0.5798(7) 0.75871(13) 0.0538(10) Uani 1 1 d . . . . .
H3 H 0.668939 0.696960 0.770183 0.065 Uiso 1 1 calc R U . . .
C4 C 0.5437(4) 0.4084(7) 0.78951(13) 0.0500(9) Uani 1 1 d . . . . .
H4 H 0.581567 0.409329 0.822341 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4377(4) 0.2353(7) 0.77177(13) 0.0531(10) Uani 1 1 d . . . . .
H5 H 0.404983 0.114490 0.792593 0.064 Uiso 1 1 calc R U . . .
C6 C 0.3773(4) 0.2344(6) 0.72349(12) 0.0446(8) Uani 1 1 d . . . . .
H6 H 0.304588 0.113488 0.712106 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3583(4) 0.4166(5) 0.64082(11) 0.0357(7) Uani 1 1 d . . . . .
C8 C 0.3849(4) 0.5796(6) 0.60772(12) 0.0384(7) Uani 1 1 d . . . . .
H8 H 0.445226 0.717327 0.616800 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3227(4) 0.5505(5) 0.55759(11) 0.0347(7) Uani 1 1 d . . . . .
C10 C 0.2252(4) 0.3472(5) 0.54579(11) 0.0324(7) Uani 1 1 d . . . . .
C11 C 0.1870(4) 0.1790(6) 0.58352(11) 0.0362(7) Uani 1 1 d . . . . .
C12 C 0.1663(4) 0.3127(6) 0.49841(11) 0.0356(7) Uani 1 1 d . . . . .
H12 H 0.099948 0.179825 0.489980 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2061(3) 0.4767(5) 0.46299(11) 0.0319(7) Uani 1 1 d . . . . .
C14 C 0.3059(4) 0.6728(5) 0.47836(11) 0.0350(7) Uani 1 1 d . . . . .
C15 C 0.3480(4) 0.8396(6) 0.44311(11) 0.0389(8) Uani 1 1 d . . . . .
H15 H 0.414160 0.971698 0.452263 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2934(4) 0.8104(6) 0.39597(12) 0.0412(8) Uani 1 1 d . . . . .
H16 H 0.323053 0.923124 0.373000 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1937(4) 0.6162(6) 0.38065(12) 0.0425(8) Uani 1 1 d . . . . .
H17 H 0.157496 0.600173 0.347848 0.051 Uiso 1 1 calc R U . . .
C18 C 0.1503(4) 0.4532(6) 0.41315(11) 0.0403(8) Uani 1 1 d . . . . .
H18 H 0.083160 0.323652 0.403026 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C7 1.385(4) . ?
O1 C11 1.387(4) . ?
O2 C11 1.191(4) . ?
N1 C9 1.313(4) . ?
N1 C14 1.369(4) . ?
C1 C6 1.381(4) . ?
C1 C2 1.390(4) . ?
C1 C7 1.488(4) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.367(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.322(4) . ?
C8 C9 1.454(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.414(4) . ?
C10 C12 1.379(4) . ?
C10 C11 1.456(4) . ?
C12 C13 1.399(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.415(4) . ?
C13 C18 1.429(4) . ?
C14 C15 1.411(4) . ?
C15 C16 1.360(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.406(5) . ?
C16 H16 0.9400 . ?
C17 C18 1.347(4) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?

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 C11 123.0(2) . . ?
C9 N1 C14 117.6(3) . . ?
C6 C1 C2 117.5(3) . . ?
C6 C1 C7 121.4(3) . . ?
C2 C1 C7 121.0(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 O1 120.8(3) . . ?
C8 C7 C1 128.0(3) . . ?
O1 C7 C1 111.2(3) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
N1 C9 C10 123.3(3) . . ?
N1 C9 C8 119.0(3) . . ?
C10 C9 C8 117.6(3) . . ?
C12 C10 C9 119.0(3) . . ?
C12 C10 C11 121.0(3) . . ?
C9 C10 C11 120.0(3) . . ?
O2 C11 O1 117.6(3) . . ?
O2 C11 C10 125.6(3) . . ?
O1 C11 C10 116.8(3) . . ?
C10 C12 C13 119.5(3) . . ?
C10 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 117.1(3) . . ?
C12 C13 C18 122.9(3) . . ?
C14 C13 C18 120.0(3) . . ?
N1 C14 C15 118.7(3) . . ?
N1 C14 C13 123.4(3) . . ?
C15 C14 C13 117.9(3) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

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
_geom_hbond_publ_flag
C15 H15 N1 0.94 2.60 3.527(4) 170.5 3_676 yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.043



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
