#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:30:01 +0200 (lun 06 de sep de 2021) $
#$Revision: 268676 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/25/7242594.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_7242594
loop_
_publ_author_name
'Sasaki, Toshiyuki'
'Ranjan, Subham'
'Takamizawa, Satoshi'
_publ_section_title
;
 A photoluminescent organosuperelastic crystal of 7-amino-4-methylcoumarin
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5801
_journal_page_last               5804
_journal_paper_doi               10.1039/D1CE00359C
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18
_chemical_name_systematic        7-Amino-4-methylcoumarin
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                71.817(6)
_cell_angle_beta                 84.968(8)
_cell_angle_gamma                70.026(8)
_cell_formula_units_Z            2
_cell_length_a                   6.9349(19)
_cell_length_b                   7.1467(15)
_cell_length_c                   9.558(2)
_cell_measurement_reflns_used    620
_cell_measurement_temperature    296
_cell_measurement_theta_max      21.245
_cell_measurement_theta_min      2.2435
_cell_volume                     422.89(17)
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service V6.2.14 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5217
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.243
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       platelet
_exptl_crystal_F_000             184
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.099
_refine_diff_density_max         1.328
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.653
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.653
_refine_ls_R_factor_all          0.2083
_refine_ls_R_factor_gt           0.1819
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4492
_refine_ls_wR_factor_ref         0.4751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                862
_reflns_number_total             1468
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00359c5.cif
_cod_data_source_block           Mother
_cod_depositor_comments
'Adding full bibliography for 7242594--7242595.cif.'
_cod_original_cell_volume        422.89(18)
_cod_database_code               7242594
_shelx_shelxl_version_number     2018/3
_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   0.980
_shelx_estimated_absorpt_t_max   0.992
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
O1 O 0.1448(6) 0.7230(6) 0.6587(4) 0.0536(14) Uani 1 1 d . . . . .
C3 C 0.3020(9) 0.2883(8) 0.7245(6) 0.0476(16) Uani 1 1 d . . . . .
C6 C 0.2038(9) 0.7009(9) 0.2845(6) 0.0475(16) Uani 1 1 d . . . . .
O2 O 0.1114(8) 0.6980(7) 0.8932(4) 0.0764(18) Uani 1 1 d . . . . .
C8 C 0.1956(8) 0.6355(8) 0.5455(5) 0.0418(15) Uani 1 1 d . . . . .
C4 C 0.3135(10) 0.3481(9) 0.4496(6) 0.0524(17) Uani 1 1 d . . . . .
H4 H 0.364491 0.205096 0.463086 0.063 Uiso 1 1 calc R U . . .
C2 C 0.2491(10) 0.3810(9) 0.8316(6) 0.0541(17) Uani 1 1 d . . . . .
H2 H 0.267610 0.296698 0.929074 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2728(9) 0.4197(8) 0.5738(6) 0.0444(16) Uani 1 1 d . . . . .
C7 C 0.1608(9) 0.7733(8) 0.4069(6) 0.0481(16) Uani 1 1 d . . . . .
H7 H 0.108117 0.916023 0.394157 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2807(10) 0.4817(9) 0.3100(6) 0.0546(18) Uani 1 1 d . . . . .
H5 H 0.308989 0.428589 0.230349 0.066 Uiso 1 1 calc R U . . .
N1 N 0.1718(9) 0.8353(9) 0.1450(5) 0.0667(18) Uani 1 1 d . . . . .
H1A H 0.124076 0.967827 0.131302 0.080 Uiso 1 1 calc R U . . .
H1B H 0.199277 0.787631 0.070748 0.080 Uiso 1 1 calc R U . . .
C1 C 0.1661(11) 0.6016(10) 0.8033(6) 0.0560(18) Uani 1 1 d . . . . .
C10 C 0.3877(12) 0.0559(9) 0.7605(7) 0.066(2) Uani 1 1 d . . . . .
H10A H 0.385321 -0.006338 0.865065 0.099 Uiso 1 1 calc R U . . .
H10B H 0.526570 0.016028 0.727773 0.099 Uiso 1 1 calc R U . . .
H10C H 0.306349 0.008825 0.711841 0.099 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'
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'
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
C1 O1 C8 121.5(4) . . ?
C2 C3 C9 118.0(5) . . ?
C2 C3 C10 121.1(5) . . ?
C9 C3 C10 120.9(5) . . ?
N1 C6 C7 121.3(5) . . ?
N1 C6 C5 121.0(5) . . ?
C7 C6 C5 117.6(5) . . ?
C7 C8 O1 115.6(5) . . ?
C7 C8 C9 123.4(5) . . ?
O1 C8 C9 121.0(5) . . ?
C5 C4 C9 122.0(5) . . ?
C5 C4 H4 119.0 . . ?
C9 C4 H4 119.0 . . ?
C3 C2 C1 123.4(5) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C8 C9 C4 116.0(5) . . ?
C8 C9 C3 118.9(5) . . ?
C4 C9 C3 125.2(5) . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O2 C1 O1 115.1(5) . . ?
O2 C1 C2 127.6(6) . . ?
O1 C1 C2 117.3(5) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 C1 1.372(7) . ?
O1 C8 1.375(6) . ?
C3 C2 1.347(8) . ?
C3 C9 1.440(7) . ?
C3 C10 1.495(8) . ?
C6 N1 1.362(7) . ?
C6 C7 1.391(8) . ?
C6 C5 1.419(8) . ?
O2 C1 1.221(7) . ?
C8 C7 1.365(7) . ?
C8 C9 1.392(8) . ?
C4 C5 1.361(8) . ?
C4 C9 1.405(8) . ?
C4 H4 0.9300 . ?
C2 C1 1.426(9) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
