#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/40/4504013.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_4504013
loop_
_publ_author_name
'Moorthy, Jarugu Narasimha'
'Venkatakrishnan, Parthasarathy'
_publ_section_title
;
 Double [2+2] Photocycloaddition:  Topochemical Conversion of
 4-Methyl-7-Styrylcoumarin Dimorphs into a Strained Cyclophane
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              713
_journal_paper_doi               10.1021/cg060652k
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C18 H14 O2'
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_chemical_melting_point          200
_chemical_name_common            4-methyl-7-styrylcoumarin
_chemical_name_systematic
;
 4-methyl-7-styrylcoumarin
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 108.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   12.866(5)
_cell_length_b                   8.321(5)
_cell_length_c                   13.307(5)
_cell_measurement_reflns_used    97
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      0
_cell_volume                     1354.9(11)
_computing_cell_refinement       'CAD-4 Enraf Nonius'
_computing_data_collection       'CAD-4 Enraf Nonius'
_computing_data_reduction        'CAD-4 Enraf Nonius'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0086
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1919
_diffrn_reflns_theta_full        22.43
_diffrn_reflns_theta_max         22.43
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0933P)²+0.9002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1878
_reflns_number_gt                1116
_reflns_number_total             1739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060652ksi20060928_013026.cif
_cod_data_source_block           4-methyl-7-styrylcoumarin(polymorph1)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4504013
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.07436(19) 0.1965(3) 0.37382(17) 0.0524(8) Uani 1 1 d .
C2 C 0.0205(3) 0.2361(4) 0.4452(3) 0.0415(9) Uani 1 1 d .
C3 C 0.0605(3) 0.1869(4) 0.5497(3) 0.0409(9) Uani 1 1 d .
O2 O 0.2074(2) 0.0742(4) 0.3332(2) 0.0758(10) Uani 1 1 d .
C5 C -0.1316(3) 0.3742(4) 0.4711(3) 0.0456(9) Uani 1 1 d .
C6 C -0.0721(3) 0.3299(4) 0.4069(3) 0.0453(9) Uani 1 1 d .
H6 H -0.0939 0.3629 0.3367 0.054 Uiso 1 1 calc R
C7 C -0.0951(3) 0.3226(5) 0.5764(3) 0.0548(11) Uani 1 1 d .
H7 H -0.1349 0.3501 0.6215 0.066 Uiso 1 1 calc R
C8 C 0.1600(3) 0.0947(4) 0.5824(3) 0.0441(9) Uani 1 1 d .
C9 C -0.2297(3) 0.4776(5) 0.4267(3) 0.0549(11) Uani 1 1 d .
H9 H -0.2452 0.5087 0.3565 0.066 Uiso 1 1 calc R
C10 C -0.2954(3) 0.5282(5) 0.4762(3) 0.0631(12) Uani 1 1 d .
H10 H -0.2798 0.4960 0.5463 0.076 Uiso 1 1 calc R
C11 C 0.2095(3) 0.0570(5) 0.5109(3) 0.0485(10) Uani 1 1 d .
H11 H 0.2738 -0.0025 0.5325 0.058 Uiso 1 1 calc R
C12 C -0.0019(3) 0.2324(5) 0.6144(3) 0.0513(10) Uani 1 1 d .
H12 H 0.0204 0.2008 0.6848 0.062 Uiso 1 1 calc R
C13 C 0.1677(3) 0.1043(5) 0.4020(3) 0.0522(10) Uani 1 1 d .
C14 C -0.3914(3) 0.6306(5) 0.4344(3) 0.0580(11) Uani 1 1 d .
C15 C -0.4331(3) 0.6732(5) 0.3275(4) 0.0680(12) Uani 1 1 d .
H15 H -0.3988 0.6368 0.2797 0.082 Uiso 1 1 calc R
C16 C -0.4448(4) 0.6869(6) 0.5016(4) 0.0766(14) Uani 1 1 d .
H16 H -0.4191 0.6586 0.5726 0.092 Uiso 1 1 calc R
C17 C 0.2073(3) 0.0458(6) 0.6970(3) 0.0661(13) Uani 1 1 d .
H17A H 0.1605 0.0832 0.7359 0.099 Uiso 1 1 calc R
H17B H 0.2786 0.0925 0.7260 0.099 Uiso 1 1 calc R
H17C H 0.2129 -0.0691 0.7018 0.099 Uiso 1 1 calc R
C18 C -0.5243(4) 0.7684(6) 0.2930(4) 0.0797(14) Uani 1 1 d .
H18 H -0.5513 0.7965 0.2221 0.096 Uiso 1 1 calc R
C19 C -0.5758(4) 0.8222(6) 0.3626(5) 0.0857(16) Uani 1 1 d .
H19 H -0.6385 0.8848 0.3387 0.103 Uiso 1 1 calc R
C20 C -0.5344(4) 0.7832(6) 0.4675(5) 0.0878(16) Uani 1 1 d .
H20 H -0.5675 0.8226 0.5155 0.105 Uiso 1 1 calc R
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
C13 O1 C2 121.9(3)
O1 C2 C6 116.1(3)
O1 C2 C3 120.7(3)
C6 C2 C3 123.1(3)
C2 C3 C12 115.5(3)
C2 C3 C8 118.7(3)
C12 C3 C8 125.7(3)
C6 C5 C7 117.7(3)
C6 C5 C9 118.7(3)
C7 C5 C9 123.6(4)
C5 C6 C2 120.6(3)
C12 C7 C5 121.4(4)
C11 C8 C3 119.0(3)
C11 C8 C17 121.6(3)
C3 C8 C17 119.5(3)
C10 C9 C5 126.4(4)
C9 C10 C14 127.2(4)
C8 C11 C13 122.8(3)
C7 C12 C3 121.6(3)
O2 C13 O1 116.7(3)
O2 C13 C11 126.5(4)
O1 C13 C11 116.8(3)
C16 C14 C15 117.7(4)
C16 C14 C10 119.1(4)
C15 C14 C10 123.2(4)
C18 C15 C14 120.3(4)
C20 C16 C14 121.9(5)
C19 C18 C15 120.4(5)
C18 C19 C20 119.6(5)
C16 C20 C19 120.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.375(4)
O1 C2 1.378(4)
C2 C6 1.383(5)
C2 C3 1.387(5)
C3 C12 1.399(5)
C3 C8 1.439(5)
O2 C13 1.205(4)
C5 C6 1.362(5)
C5 C7 1.401(5)
C5 C9 1.490(5)
C7 C12 1.373(5)
C8 C11 1.336(5)
C8 C17 1.512(5)
C9 C10 1.292(5)
C10 C14 1.462(6)
C11 C13 1.436(5)
C14 C16 1.368(6)
C14 C15 1.402(6)
C15 C18 1.372(6)
C16 C20 1.361(6)
C18 C19 1.369(6)
C19 C20 1.371(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29337418
2 PubChem 101732164
