#------------------------------------------------------------------------------
#$Date: 2019-11-04 10:12:53 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/38/4033874.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_4033874
loop_
_publ_author_name
'Mukhopadhyay, Arindam'
'Jana, Kanyashree'
'Hossen, Tousif'
'Sahu, Kalyanasis'
'Moorthy, Jarugu Narasimha'
_publ_section_title
;
 Coumarin-Annelated Regioisomeric Heptahelicenes: Influence of Helicity on
 Excited-State Properties and Chiroptical Properties.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10658
_journal_page_last               10668
_journal_paper_doi               10.1021/acs.joc.9b01126
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C31 H16 F3 O4'
_chemical_formula_weight         509.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 107.9150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3004(5)
_cell_length_b                   26.5371(11)
_cell_length_c                   7.3874(3)
_cell_measurement_reflns_used    4866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.349
_cell_measurement_theta_min      2.886
_cell_volume                     2294.45(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17462
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_min         2.886
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2049 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5724
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0497
_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)+(0.0510P)²+1.7480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1146
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4866
_reflns_number_total             5724
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01126_si_002.cif
_cod_data_source_block           7-in
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4033874
_shelx_shelxl_version_number     2017/1
_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, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
O001 O 0.61131(17) 0.64565(8) 0.6508(3) 0.0172(4) Uani 1 1 d . .
O002 O 0.45747(19) 0.69092(9) 0.6202(3) 0.0260(5) Uani 1 1 d . .
F003 F 0.04054(19) 0.59197(10) 0.4284(4) 0.0510(7) Uani 1 1 d . .
O004 O 0.3298(2) 0.61378(9) 0.5924(4) 0.0308(6) Uani 1 1 d . .
F005 F 0.1683(3) 0.55837(13) 0.6561(5) 0.0788(11) Uani 1 1 d . .
O006 O 0.1942(3) 0.65676(11) 0.3763(5) 0.0516(9) Uani 1 1 d . .
F007 F 0.1616(3) 0.54104(11) 0.3757(7) 0.0964(14) Uani 1 1 d . .
C008 C 0.5620(3) 0.69018(12) 0.6689(4) 0.0189(6) Uani 1 1 d . .
C009 C 0.7279(2) 0.63957(12) 0.7010(4) 0.0170(6) Uani 1 1 d . .
C00A C 0.5936(3) 0.56407(12) 0.3834(4) 0.0178(6) Uani 1 1 d . .
C00B C 0.7988(3) 0.67804(13) 0.7954(4) 0.0201(7) Uani 1 1 d . .
C00C C 0.5174(3) 0.52263(12) 0.3223(5) 0.0226(7) Uani 1 1 d . .
C00D C 0.5591(3) 0.61173(12) 0.2874(4) 0.0182(6) Uani 1 1 d . .
C00E C 0.6350(3) 0.73207(12) 0.7457(4) 0.0227(7) Uani 1 1 d . .
H00E H 0.603483 0.763704 0.750547 0.027 Uiso 1 1 calc R U
C00F C 0.6990(3) 0.55471(12) 0.5323(4) 0.0191(6) Uani 1 1 d . .
C00G C 0.7487(3) 0.72580(13) 0.8106(5) 0.0229(7) Uani 1 1 d . .
H00G H 0.795347 0.752785 0.866034 0.027 Uiso 1 1 calc R U
C00H C 0.3653(3) 0.57807(14) 0.1541(5) 0.0279(8) Uani 1 1 d . .
H00H H 0.287952 0.583366 0.092384 0.033 Uiso 1 1 calc R U
C00I C 0.4425(3) 0.61954(12) 0.1912(4) 0.0223(7) Uani 1 1 d . .
C00J C 0.7684(3) 0.59256(12) 0.6583(4) 0.0186(6) Uani 1 1 d . .
C00K C 0.8847(3) 0.58239(14) 0.7577(4) 0.0240(7) Uani 1 1 d . .
C00L C 0.2281(3) 0.62176(13) 0.4778(5) 0.0282(8) Uani 1 1 d . .
C00M C 0.6375(3) 0.65201(11) 0.2775(4) 0.0179(6) Uani 1 1 d . .
C00N C 0.4039(3) 0.53106(13) 0.2081(5) 0.0277(8) Uani 1 1 d . .
H00N H 0.354757 0.503783 0.169325 0.033 Uiso 1 1 calc R U
C00O C 0.5932(3) 0.70108(13) 0.2223(4) 0.0231(7) Uani 1 1 d . .
C00P C 0.5564(3) 0.47263(13) 0.3743(5) 0.0274(8) Uani 1 1 d . .
H00P H 0.505951 0.445783 0.336013 0.033 Uiso 1 1 calc R U
C00Q C 0.4012(3) 0.66877(13) 0.1277(5) 0.0281(8) Uani 1 1 d . .
H00Q H 0.323470 0.673567 0.067921 0.034 Uiso 1 1 calc R U
C00R C 0.4725(3) 0.70827(13) 0.1530(5) 0.0269(7) Uani 1 1 d . .
H00R H 0.442958 0.740609 0.125025 0.032 Uiso 1 1 calc R U
C00S C 0.7397(3) 0.50464(12) 0.5618(5) 0.0232(7) Uani 1 1 d . .
C00T C 0.9260(3) 0.53200(14) 0.7580(5) 0.0283(8) Uani 1 1 d . .
H00T H 1.002857 0.524980 0.817195 0.034 Uiso 1 1 calc R U
C00U C 0.6652(3) 0.46378(12) 0.4780(5) 0.0269(8) Uani 1 1 d . .
H00U H 0.692308 0.430857 0.495536 0.032 Uiso 1 1 calc R U
C00V C 0.7558(3) 0.64433(12) 0.3086(4) 0.0207(6) Uani 1 1 d . .
H00V H 0.785942 0.612023 0.333709 0.025 Uiso 1 1 calc R U
C00W C 0.9569(3) 0.62108(14) 0.8604(5) 0.0271(8) Uani 1 1 d . .
H00W H 1.033464 0.613934 0.921127 0.033 Uiso 1 1 calc R U
C00X C 0.7836(3) 0.73299(13) 0.2651(5) 0.0290(8) Uani 1 1 d . .
H00X H 0.832583 0.759869 0.267946 0.035 Uiso 1 1 calc R U
C00Y C 0.6694(3) 0.74086(13) 0.2249(5) 0.0288(8) Uani 1 1 d . .
H00Y H 0.640796 0.773393 0.198460 0.035 Uiso 1 1 calc R U
C00Z C 0.9176(3) 0.66811(14) 0.8725(5) 0.0269(7) Uani 1 1 d . .
H00Z H 0.967812 0.693704 0.930866 0.032 Uiso 1 1 calc R U
C010 C 0.8266(3) 0.68378(14) 0.3022(4) 0.0266(7) Uani 1 1 d . .
H010 H 0.903980 0.677857 0.322592 0.032 Uiso 1 1 calc R U
C011 C 0.8542(3) 0.49468(14) 0.6732(5) 0.0285(8) Uani 1 1 d . .
H011 H 0.880269 0.461568 0.687922 0.034 Uiso 1 1 calc R U
C012 C 0.1471(3) 0.57784(14) 0.4818(7) 0.0388(9) 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'
F F 0.0171 0.0103 '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
C008 O001 C009 122.5(2)
O002 C008 O001 116.5(3)
O002 C008 C00E 125.3(3)
O001 C008 C00E 118.2(3)
O001 C009 C00B 119.5(3)
O001 C009 C00J 116.9(3)
C00B C009 C00J 123.6(3)
C00C C00A C00F 117.3(3)
C00C C00A C00D 117.0(3)
C00F C00A C00D 125.7(3)
C009 C00B C00Z 118.4(3)
C009 C00B C00G 118.3(3)
C00Z C00B C00G 123.2(3)
C00N C00C C00P 120.0(3)
C00N C00C C00A 120.1(3)
C00P C00C C00A 120.0(3)
C00I C00D C00A 118.4(3)
C00I C00D C00M 117.0(3)
C00A C00D C00M 124.5(3)
C00G C00E C008 120.2(3)
C00G C00E H00E 119.9
C008 C00E H00E 119.9
C00S C00F C00A 118.2(3)
C00S C00F C00J 116.1(3)
C00A C00F C00J 125.6(3)
C00E C00G C00B 120.6(3)
C00E C00G H00G 119.7
C00B C00G H00G 119.7
C00N C00H C00I 120.2(3)
C00N C00H H00H 119.9
C00I C00H H00H 119.9
C00D C00I C00H 120.0(3)
C00D C00I C00Q 120.3(3)
C00H C00I C00Q 119.7(3)
C009 C00J C00K 114.9(3)
C009 C00J C00F 125.1(3)
C00K C00J C00F 120.0(3)
C00W C00K C00J 120.4(3)
C00W C00K C00T 120.9(3)
C00J C00K C00T 118.7(3)
O006 C00L O004 128.6(3)
O006 C00L C012 120.1(4)
O004 C00L C012 111.4(3)
C00V C00M C00O 117.5(3)
C00V C00M C00D 123.3(3)
C00O C00M C00D 119.0(3)
C00H C00N C00C 121.1(3)
C00H C00N H00N 119.4
C00C C00N H00N 119.4
C00Y C00O C00M 119.2(3)
C00Y C00O C00R 121.3(3)
C00M C00O C00R 119.3(3)
C00U C00P C00C 120.8(3)
C00U C00P H00P 119.6
C00C C00P H00P 119.6
C00R C00Q C00I 121.2(3)
C00R C00Q H00Q 119.4
C00I C00Q H00Q 119.4
C00Q C00R C00O 120.6(3)
C00Q C00R H00R 119.7
C00O C00R H00R 119.7
C00F C00S C011 120.4(3)
C00F C00S C00U 119.7(3)
C011 C00S C00U 119.9(3)
C011 C00T C00K 120.3(3)
C011 C00T H00T 119.8
C00K C00T H00T 119.8
C00P C00U C00S 120.5(3)
C00P C00U H00U 119.7
C00S C00U H00U 119.7
C010 C00V C00M 121.1(3)
C010 C00V H00V 119.5
C00M C00V H00V 119.5
C00Z C00W C00K 121.8(3)
C00Z C00W H00W 119.1
C00K C00W H00W 119.1
C00Y C00X C010 119.2(3)
C00Y C00X H00X 120.4
C010 C00X H00X 120.4
C00X C00Y C00O 121.8(3)
C00X C00Y H00Y 119.1
C00O C00Y H00Y 119.1
C00W C00Z C00B 119.3(3)
C00W C00Z H00Z 120.3
C00B C00Z H00Z 120.3
C00V C010 C00X 120.7(3)
C00V C010 H010 119.6
C00X C010 H010 119.6
C00T C011 C00S 121.6(3)
C00T C011 H011 119.2
C00S C011 H011 119.2
F007 C012 F003 110.3(4)
F007 C012 F005 105.6(4)
F003 C012 F005 106.4(3)
F007 C012 C00L 110.3(3)
F003 C012 C00L 111.9(3)
F005 C012 C00L 112.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O001 C008 1.353(4)
O001 C009 1.376(3)
O002 C008 1.225(4)
F003 C012 1.302(5)
O004 C00L 1.294(4)
F005 C012 1.336(5)
O006 C00L 1.186(4)
F007 C012 1.299(5)
C008 C00E 1.431(4)
C009 C00B 1.384(4)
C009 C00J 1.414(4)
C00A C00C 1.426(4)
C00A C00F 1.440(4)
C00A C00D 1.448(4)
C00B C00Z 1.420(5)
C00B C00G 1.428(5)
C00C C00N 1.409(5)
C00C C00P 1.423(5)
C00D C00I 1.407(4)
C00D C00M 1.456(4)
C00E C00G 1.343(5)
C00E H00E 0.9300
C00F C00S 1.413(4)
C00F C00J 1.454(4)
C00G H00G 0.9300
C00H C00N 1.351(5)
C00H C00I 1.424(5)
C00H H00H 0.9300
C00I C00Q 1.428(5)
C00J C00K 1.419(4)
C00K C00W 1.416(5)
C00K C00T 1.430(5)
C00L C012 1.540(5)
C00M C00V 1.416(4)
C00M C00O 1.422(4)
C00N H00N 0.9300
C00O C00Y 1.407(5)
C00O C00R 1.427(5)
C00P C00U 1.342(5)
C00P H00P 0.9300
C00Q C00R 1.343(5)
C00Q H00Q 0.9300
C00R H00R 0.9300
C00S C011 1.421(5)
C00S C00U 1.432(5)
C00T C011 1.346(5)
C00T H00T 0.9300
C00U H00U 0.9300
C00V C010 1.372(5)
C00V H00V 0.9300
C00W C00Z 1.351(5)
C00W H00W 0.9300
C00X C00Y 1.360(6)
C00X C010 1.404(5)
C00X H00X 0.9300
C00Y H00Y 0.9300
C00Z H00Z 0.9300
C010 H010 0.9300
C011 H011 0.9300
