#------------------------------------------------------------------------------
#$Date: 2017-06-16 07:59:25 +0300 (Fri, 16 Jun 2017) $
#$Revision: 197884 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/85/7228502.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_7228502
loop_
_publ_author_name
'Pessêgo, Márcia'
'Basílio, Nuno'
'Mendoza, Johan'
'Avó, João'
'Cunha-Silva, Luís'
'Parola, A. Jorge'
'Pina, Fernando'
_publ_section_title
;
 Exploring the diethylaminoflavylium derivatives multistate system of
 chemical reactions in the presence of CTAB micelles: thermodynamic
 reversibility achieved through different kinetic pathways
;
_journal_issue                   48
_journal_name_full               'RSC Adv.'
_journal_page_first              30469
_journal_paper_doi               10.1039/C7RA04514J
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C21 H22 N O, B F4'
_chemical_formula_sum            'C21 H22 B F4 N O'
_chemical_formula_weight         391.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             '23 January 2017'
_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_audit_update_record
;
2017-04-10 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.893(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6076(16)
_cell_length_b                   17.9505(12)
_cell_length_c                   14.4826(13)
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.86
_cell_volume                     3708.2(6)
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19043
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.649
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0495
_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)+(0.0478P)²+4.0538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2538
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ra04514j2.cif
_cod_data_source_block           comp1
_cod_original_cell_volume        3708.2(5)
_cod_database_code               7228502
_shelx_shelxl_version_number     2014/7
_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   0.978
_shelx_estimated_absorpt_t_max   0.989
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'
'-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
_atom_site_refinement_flags_occupancy
O1 O 0.03482(10) 0.00746(7) 0.66835(11) 0.0261(3) Uani 1 1 d . . .
N1 N 0.32015(12) -0.09139(9) 0.98572(14) 0.0290(4) Uani 1 1 d . . .
C1 C 0.4854(2) -0.1021(2) 1.0549(3) 0.0888(12) Uani 1 1 d . U .
H1A H 0.4752 -0.1531 1.0260 0.133 Uiso 1 1 calc R U .
H1B H 0.5499 -0.0969 1.1233 0.133 Uiso 1 1 calc R U .
H1C H 0.4749 -0.0672 0.9964 0.133 Uiso 1 1 calc R U .
C2 C 0.41892(15) -0.08519(12) 1.08403(19) 0.0367(5) Uani 1 1 d . . .
H2A H 0.4309 -0.1199 1.1443 0.044 Uiso 1 1 calc R U .
H2B H 0.4308 -0.0340 1.1151 0.044 Uiso 1 1 calc R U .
C3 C 0.28074(16) -0.16696(11) 0.96072(18) 0.0322(5) Uani 1 1 d . . .
H3A H 0.2153 -0.1642 0.9367 0.039 Uiso 1 1 calc R U .
H3B H 0.3170 -0.1971 1.0314 0.039 Uiso 1 1 calc R U .
C4 C 0.28155(18) -0.20624(13) 0.8682(2) 0.0465(6) Uani 1 1 d . . .
H4A H 0.2455 -0.1770 0.7977 0.070 Uiso 1 1 calc R U .
H4B H 0.2534 -0.2558 0.8545 0.070 Uiso 1 1 calc R U .
H4C H 0.3463 -0.2113 0.8927 0.070 Uiso 1 1 calc R U .
C5 C 0.26871(14) -0.03311(11) 0.92053(17) 0.0269(5) Uani 1 1 d . . .
C6 C 0.30749(15) 0.04146(11) 0.94853(18) 0.0308(5) Uani 1 1 d . . .
H6 H 0.3705 0.0489 1.0126 0.037 Uiso 1 1 calc R U .
C7 C 0.25551(16) 0.10065(11) 0.88499(18) 0.0329(5) Uani 1 1 d . . .
H7 H 0.2828 0.1489 0.9065 0.039 Uiso 1 1 calc R U .
C8 C 0.16144(15) 0.09311(11) 0.78711(18) 0.0285(5) Uani 1 1 d . . .
C9 C 0.12522(14) 0.01888(10) 0.76110(16) 0.0254(4) Uani 1 1 d . . .
C10 C 0.17491(14) -0.04193(11) 0.82400(17) 0.0267(4) Uani 1 1 d . . .
H10 H 0.1468 -0.0899 0.8032 0.032 Uiso 1 1 calc R U .
C11 C 0.10485(15) 0.15009(11) 0.71462(18) 0.0312(5) Uani 1 1 d . . .
H11 H 0.1277 0.1998 0.7319 0.037 Uiso 1 1 calc R U .
C12 C 0.01504(15) 0.13606(11) 0.61679(18) 0.0296(5) Uani 1 1 d . . .
C13 C -0.01820(15) 0.06392(10) 0.59688(16) 0.0263(4) Uani 1 1 d . . .
C14 C -0.11082(15) 0.04193(11) 0.50052(17) 0.0275(5) Uani 1 1 d . . .
C15 C -0.17647(16) 0.09886(11) 0.43603(18) 0.0303(5) Uani 1 1 d . . .
C16 C -0.14954(16) 0.17906(11) 0.47312(19) 0.0373(5) Uani 1 1 d . . .
H16A H -0.1637 0.1916 0.5281 0.045 Uiso 1 1 calc R U .
H16B H -0.1879 0.2119 0.4060 0.045 Uiso 1 1 calc R U .
C17 C -0.04625(16) 0.19408(11) 0.52810(19) 0.0359(5) Uani 1 1 d . . .
H17A H -0.0350 0.1940 0.4687 0.043 Uiso 1 1 calc R U .
H17B H -0.0295 0.2439 0.5642 0.043 Uiso 1 1 calc R U .
C18 C -0.13660(15) -0.03320(11) 0.47189(17) 0.0292(5) Uani 1 1 d . . .
H18 H -0.0926 -0.0716 0.5158 0.035 Uiso 1 1 calc R U .
C19 C -0.22630(15) -0.05074(12) 0.37949(18) 0.0324(5) Uani 1 1 d . . .
H19 H -0.2438 -0.1014 0.3592 0.039 Uiso 1 1 calc R U .
C20 C -0.29094(16) 0.00530(12) 0.31613(18) 0.0351(5) Uani 1 1 d . . .
H20 H -0.3525 -0.0072 0.2527 0.042 Uiso 1 1 calc R U .
C21 C -0.26624(16) 0.07919(12) 0.34475(18) 0.0353(5) Uani 1 1 d . . .
H21 H -0.3114 0.1170 0.3013 0.042 Uiso 1 1 calc R U .
F1 F -0.03739(16) -0.17612(12) 0.6545(2) 0.1137(9) Uani 1 1 d . U .
F2 F -0.06897(11) -0.26224(9) 0.73807(15) 0.0706(5) Uani 1 1 d . . .
B1 B 0.0000 -0.2184(2) 0.7500 0.0395(9) Uani 1 2 d S T P
F3 F 0.42064(11) 0.19782(8) 0.19085(16) 0.0721(5) Uani 1 1 d . . .
F4 F 0.50369(12) 0.11052(12) 0.17629(16) 0.0945(7) Uani 1 1 d . U .
B2 B 0.5000 0.15417(19) 0.2500 0.0359(8) Uani 1 2 d S T P
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
C13 O1 C9 121.43(15) . .
C5 N1 C3 121.31(17) . .
C5 N1 C2 123.31(17) . .
C3 N1 C2 115.36(16) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C1 113.0(2) . .
N1 C2 H2A 109.0 . .
C1 C2 H2A 109.0 . .
N1 C2 H2B 109.0 . .
C1 C2 H2B 109.0 . .
H2A C2 H2B 107.8 . .
N1 C3 C4 113.45(18) . .
N1 C3 H3A 108.9 . .
C4 C3 H3A 108.9 . .
N1 C3 H3B 108.9 . .
C4 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
N1 C5 C10 121.55(18) . .
N1 C5 C6 120.68(19) . .
C10 C5 C6 117.76(18) . .
C7 C6 C5 121.1(2) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
C6 C7 C8 122.18(19) . .
C6 C7 H7 118.9 . .
C8 C7 H7 118.9 . .
C11 C8 C7 125.90(19) . .
C11 C8 C9 118.53(19) . .
C7 C8 C9 115.52(18) . .
C10 C9 O1 117.27(17) . .
C10 C9 C8 123.98(19) . .
O1 C9 C8 118.74(17) . .
C9 C10 C5 119.46(18) . .
C9 C10 H10 120.3 . .
C5 C10 H10 120.3 . .
C8 C11 C12 121.37(18) . .
C8 C11 H11 119.3 . .
C12 C11 H11 119.3 . .
C13 C12 C11 118.11(18) . .
C13 C12 C17 117.78(19) . .
C11 C12 C17 124.03(18) . .
O1 C13 C12 121.62(19) . .
O1 C13 C14 114.50(17) . .
C12 C13 C14 123.88(18) . .
C18 C14 C15 120.2(2) . .
C18 C14 C13 122.18(18) . .
C15 C14 C13 117.64(18) . .
C21 C15 C14 118.75(19) . .
C21 C15 C16 121.74(19) . .
C14 C15 C16 119.4(2) . .
C15 C16 C17 112.59(18) . .
C15 C16 H16A 109.1 . .
C17 C16 H16A 109.1 . .
C15 C16 H16B 109.1 . .
C17 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
C12 C17 C16 111.24(17) . .
C12 C17 H17A 109.4 . .
C16 C17 H17A 109.4 . .
C12 C17 H17B 109.4 . .
C16 C17 H17B 109.4 . .
H17A C17 H17B 108.0 . .
C19 C18 C14 119.52(19) . .
C19 C18 H18 120.2 . .
C14 C18 H18 120.2 . .
C18 C19 C20 120.3(2) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C21 C20 C19 120.4(2) . .
C21 C20 H20 119.8 . .
C19 C20 H20 119.8 . .
C20 C21 C15 120.9(2) . .
C20 C21 H21 119.6 . .
C15 C21 H21 119.6 . .
F1 B1 F1 112.2(3) 2_556 .
F1 B1 F2 108.27(11) 2_556 .
F1 B1 F2 109.08(13) . .
F1 B1 F2 109.08(13) 2_556 2_556
F1 B1 F2 108.26(11) . 2_556
F2 B1 F2 109.9(3) . 2_556
F4 B2 F4 109.4(3) 2_655 .
F4 B2 F3 109.79(11) 2_655 2_655
F4 B2 F3 108.60(11) . 2_655
F4 B2 F3 108.60(11) 2_655 .
F4 B2 F3 109.79(11) . .
F3 B2 F3 110.7(3) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.355(2) .
O1 C9 1.369(2) .
N1 C5 1.343(3) .
N1 C3 1.469(3) .
N1 C2 1.470(3) .
C1 C2 1.489(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.522(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C10 1.414(3) .
C5 C6 1.448(3) .
C6 C7 1.351(3) .
C6 H6 0.9500 .
C7 C8 1.421(3) .
C7 H7 0.9500 .
C8 C11 1.384(3) .
C8 C9 1.429(3) .
C9 C10 1.361(3) .
C10 H10 0.9500 .
C11 C12 1.394(3) .
C11 H11 0.9500 .
C12 C13 1.380(3) .
C12 C17 1.508(3) .
C13 C14 1.447(3) .
C14 C18 1.406(3) .
C14 C15 1.410(3) .
C15 C21 1.386(3) .
C15 C16 1.512(3) .
C16 C17 1.522(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.381(3) .
C18 H18 0.9500 .
C19 C20 1.387(3) .
C19 H19 0.9500 .
C20 C21 1.382(3) .
C20 H20 0.9500 .
C21 H21 0.9500 .
F1 B1 1.361(3) .
F2 B1 1.370(3) .
B1 F1 1.361(3) 2_556
B1 F2 1.370(3) 2_556
F3 B2 1.377(2) .
F4 B2 1.356(2) .
B2 F4 1.356(2) 2_655
B2 F3 1.377(2) 2_655
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
C2 H2A F2 0.99 2.51 3.459(3) 159.9 8_546
C3 H3A F1 0.99 2.60 3.576(3) 169.0 2_556
C3 H3B F2 0.99 2.55 3.506(3) 163.4 8_546
C6 H6 F4 0.95 2.41 3.315(3) 158.4 1_556
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
C5 N1 C2 C1 -94.7(3)
C3 N1 C2 C1 83.9(3)
C5 N1 C3 C4 81.6(2)
C2 N1 C3 C4 -97.0(2)
C3 N1 C5 C10 -1.0(3)
C2 N1 C5 C10 177.52(18)
C3 N1 C5 C6 177.84(18)
C2 N1 C5 C6 -3.6(3)
N1 C5 C6 C7 -178.41(19)
C10 C5 C6 C7 0.5(3)
C5 C6 C7 C8 -1.1(3)
C6 C7 C8 C11 -176.9(2)
C6 C7 C8 C9 0.6(3)
C13 O1 C9 C10 -176.06(16)
C13 O1 C9 C8 4.7(3)
C11 C8 C9 C10 178.15(19)
C7 C8 C9 C10 0.4(3)
C11 C8 C9 O1 -2.7(3)
C7 C8 C9 O1 179.59(17)
O1 C9 C10 C5 179.84(16)
C8 C9 C10 C5 -1.0(3)
N1 C5 C10 C9 179.38(18)
C6 C5 C10 C9 0.5(3)
C7 C8 C11 C12 176.2(2)
C9 C8 C11 C12 -1.3(3)
C8 C11 C12 C13 3.3(3)
C8 C11 C12 C17 -173.41(19)
C9 O1 C13 C12 -2.7(3)
C9 O1 C13 C14 177.60(16)
C11 C12 C13 O1 -1.3(3)
C17 C12 C13 O1 175.59(17)
C11 C12 C13 C14 178.31(18)
C17 C12 C13 C14 -4.8(3)
O1 C13 C14 C18 -11.7(3)
C12 C13 C14 C18 168.66(19)
O1 C13 C14 C15 167.12(16)
C12 C13 C14 C15 -12.6(3)
C18 C14 C15 C21 0.1(3)
C13 C14 C15 C21 -178.68(18)
C18 C14 C15 C16 175.71(18)
C13 C14 C15 C16 -3.1(3)
C21 C15 C16 C17 -151.03(19)
C14 C15 C16 C17 33.5(3)
C13 C12 C17 C16 35.1(3)
C11 C12 C17 C16 -148.2(2)
C15 C16 C17 C12 -48.0(2)
C15 C14 C18 C19 0.7(3)
C13 C14 C18 C19 179.45(18)
C14 C18 C19 C20 -0.8(3)
C18 C19 C20 C21 0.0(3)
C19 C20 C21 C15 0.8(3)
C14 C15 C21 C20 -0.9(3)
C16 C15 C21 C20 -176.35(19)
