#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/21/7122186.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_7122186
loop_
_publ_author_name
'Huang, Huan-Ming'
'Adams, Ralph W.'
'Procter, David J.'
_publ_section_title
;
 Reductive cyclisations of amidines involving aminal radicals.
;
_journal_issue                   72
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10160
_journal_page_last               10163
_journal_paper_doi               10.1039/c8cc05178j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H20 N2 O'
_chemical_formula_sum            'C19 H20 N2 O'
_chemical_formula_weight         292.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2018-05-31 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   41.133(3)
_cell_length_b                   13.3359(14)
_cell_length_c                   11.1564(8)
_cell_measurement_reflns_used    5845
_cell_measurement_temperature    149.9(4)
_cell_measurement_theta_max      26.5890
_cell_measurement_theta_min      3.7410
_cell_volume                     6119.8(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  51.00   1.00   22.50    --   20.18  57.00   0.00   52
  2  ω    -49.00  52.00   1.00   22.50    --   20.18 -77.00  30.00  101
  3  ω    -42.00  52.00   1.00   22.50    --   20.18 -77.00 150.00   94
  4  ω      1.00  82.00   1.00   22.50    --   20.18  37.00 -60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169092000
_diffrn_orient_matrix_UB_12      0.0104263000
_diffrn_orient_matrix_UB_13      0.0028203000
_diffrn_orient_matrix_UB_21      -0.0033963000
_diffrn_orient_matrix_UB_22      0.0520813000
_diffrn_orient_matrix_UB_23      0.0029939000
_diffrn_orient_matrix_UB_31      -0.0005942000
_diffrn_orient_matrix_UB_32      -0.0026641000
_diffrn_orient_matrix_UB_33      0.0634021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19398
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.136
_diffrn_reflns_theta_min         3.212
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.635
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0785
_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)+(0.1370P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2542
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                4664
_reflns_number_total             7118
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc05178j2.cif
_cod_data_source_block           adjp201
_cod_depositor_comments
'Adding full bibliography for 7122184--7122186.cif.'
_cod_database_code               7122186
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H30N2O3
_chemical_oxdiff_usercomment     'astl 61 oaw1 aw/stl'
_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.
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00H(H00C,H00E), C00J(H00H,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C10(H10), C7(H7), C6(H6), C00D(H00D), C00F(H00F), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2017-03-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.632
_oxdiff_exptl_absorpt_empirical_full_min 0.403
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
O001 O 0.71956(7) 0.3392(2) 0.3958(3) 0.0356(7) Uani 1 1 d .
N4 N 0.72130(8) 0.5045(3) 0.0981(3) 0.0350(8) Uani 1 1 d .
H4 H 0.7305 0.5539 0.0620 0.042 Uiso 1 1 calc R
N003 N 0.73584(8) 0.3570(2) 0.2037(3) 0.0270(8) Uani 1 1 d .
C004 C 0.69446(9) 0.5167(2) 0.1766(4) 0.0260(9) Uani 1 1 d .
C005 C 0.71536(9) 0.3768(3) 0.2938(4) 0.0248(8) Uani 1 1 d .
C10 C 0.80710(9) 0.3842(3) -0.2183(4) 0.0288(9) Uani 1 1 d .
H10 H 0.7879 0.3535 -0.2423 0.035 Uiso 1 1 calc R
C7 C 0.67281(10) 0.5982(3) 0.1605(4) 0.0355(10) Uani 1 1 d .
H7 H 0.6767 0.6444 0.0998 0.043 Uiso 1 1 calc R
C6 C 0.66236(9) 0.4513(3) 0.3424(4) 0.0311(10) Uani 1 1 d .
H6 H 0.6584 0.4020 0.3995 0.037 Uiso 1 1 calc R
C9 C 0.80474(11) 0.4492(3) -0.1251(4) 0.0374(11) Uani 1 1 d .
C8 C 0.70536(10) 0.3416(3) 0.0099(4) 0.0336(9) Uani 1 1 d .
H8A H 0.6839 0.3616 0.0338 0.050 Uiso 1 1 calc GR
H8B H 0.7082 0.2713 0.0253 0.050 Uiso 1 1 calc GR
H8C H 0.7082 0.3544 -0.0741 0.050 Uiso 1 1 calc GR
C00B C 0.68997(10) 0.4472(3) 0.2672(4) 0.0289(9) Uani 1 1 d .
C00C C 0.73157(11) 0.4039(3) 0.0844(3) 0.0305(10) Uani 1 1 d .
C00D C 0.83443(11) 0.5040(3) -0.1006(4) 0.0384(11) Uani 1 1 d .
H00D H 0.8342 0.5565 -0.0458 0.046 Uiso 1 1 calc R
C00E C 0.77409(10) 0.4685(3) -0.0583(4) 0.0344(10) Uani 1 1 d .
H00A H 0.7762 0.5320 -0.0166 0.041 Uiso 1 1 calc R
H00B H 0.7565 0.4754 -0.1159 0.041 Uiso 1 1 calc R
C00F C 0.83380(11) 0.3592(3) -0.2795(4) 0.0364(11) Uani 1 1 d .
H00F H 0.8330 0.3080 -0.3360 0.044 Uiso 1 1 calc R
C00G C 0.76537(10) 0.3949(3) 0.0251(4) 0.0338(10) Uani 1 1 d .
H00G H 0.7643 0.3328 -0.0216 0.041 Uiso 1 1 calc R
C00H C 0.79021(11) 0.3723(3) 0.1264(4) 0.0403(11) Uani 1 1 d .
H00C H 0.7985 0.4336 0.1618 0.048 Uiso 1 1 calc R
H00E H 0.8083 0.3324 0.0971 0.048 Uiso 1 1 calc R
C00I C 0.64629(9) 0.6098(3) 0.2330(4) 0.0359(10) Uani 1 1 d .
H00I H 0.6323 0.6640 0.2225 0.043 Uiso 1 1 calc R
C00J C 0.76922(10) 0.3124(3) 0.2173(5) 0.0416(12) Uani 1 1 d .
H00H H 0.7691 0.2415 0.1980 0.050 Uiso 1 1 calc R
H00J H 0.7773 0.3211 0.2984 0.050 Uiso 1 1 calc R
C00K C 0.64021(11) 0.5363(3) 0.3270(3) 0.0399(11) Uani 1 1 d .
H00K H 0.6223 0.5434 0.3771 0.048 Uiso 1 1 calc R
C00L C 0.86339(12) 0.4788(4) -0.1584(5) 0.0557(15) Uani 1 1 d .
H00L H 0.8828 0.5065 -0.1309 0.067 Uiso 1 1 calc R
C00M C 0.86430(11) 0.4121(3) -0.2579(5) 0.0530(14) Uani 1 1 d .
H00M H 0.8827 0.4031 -0.3051 0.064 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'
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
C004 N4 H4 123.0
C004 N4 C00C 114.1(3)
C00C N4 H4 123.0
C005 N003 C00C 121.1(3)
C005 N003 C00J 125.2(4)
C00C N003 C00J 111.5(3)
C7 C004 N4 120.0(4)
C00B C004 N4 118.5(3)
C00B C004 C7 121.5(4)
O001 C005 N003 121.0(3)
O001 C005 C00B 123.3(4)
N003 C005 C00B 115.6(4)
C9 C10 H10 116.2
C00F C10 H10 116.2
C00F C10 C9 127.6(4)
C004 C7 H7 119.5
C00I C7 C004 121.0(4)
C00I C7 H7 119.5
C00B C6 H6 121.3
C00B C6 C00K 117.4(4)
C00K C6 H6 121.3
C10 C9 C00D 114.0(4)
C10 C9 C00E 123.7(4)
C00D C9 C00E 122.2(4)
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C00C C8 H8A 109.5
C00C C8 H8B 109.5
C00C C8 H8C 109.5
C004 C00B C005 119.5(4)
C004 C00B C6 121.0(4)
C6 C00B C005 119.2(4)
N4 C00C N003 109.8(3)
N4 C00C C8 110.4(4)
N4 C00C C00G 112.8(3)
N003 C00C C8 109.2(3)
N003 C00C C00G 104.2(3)
C00G C00C C8 110.2(3)
C9 C00D H00D 119.6
C00L C00D C9 120.7(4)
C00L C00D H00D 119.6
C9 C00E H00A 108.4
C9 C00E H00B 108.4
H00A C00E H00B 107.5
C00G C00E C9 115.4(4)
C00G C00E H00A 108.4
C00G C00E H00B 108.4
C10 C00F H00F 119.9
C10 C00F C00M 120.1(4)
C00M C00F H00F 119.9
C00C C00G H00G 104.6
C00C C00G C00H 107.1(3)
C00E C00G C00C 117.5(4)
C00E C00G H00G 104.6
C00E C00G C00H 116.9(4)
C00H C00G H00G 104.6
C00G C00H H00C 111.3
C00G C00H H00E 111.3
C00G C00H C00J 102.1(4)
H00C C00H H00E 109.2
C00J C00H H00C 111.3
C00J C00H H00E 111.3
C7 C00I H00I 120.5
C7 C00I C00K 119.1(4)
C00K C00I H00I 120.5
N003 C00J C00H 103.8(3)
N003 C00J H00H 111.0
N003 C00J H00J 111.0
C00H C00J H00H 111.0
C00H C00J H00J 111.0
H00H C00J H00J 109.0
C6 C00K H00K 120.1
C00I C00K C6 119.9(4)
C00I C00K H00K 120.1
C00D C00L H00L 118.9
C00D C00L C00M 122.2(4)
C00M C00L H00L 118.9
C00F C00M H00M 123.0
C00L C00M C00F 114.1(4)
C00L C00M H00M 123.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O001 C005 1.255(5)
N4 H4 0.8600
N4 C004 1.419(5)
N4 C00C 1.415(5)
N003 C005 1.338(5)
N003 C00C 1.481(5)
N003 C00J 1.504(5)
C004 C7 1.416(5)
C004 C00B 1.385(5)
C005 C00B 1.435(5)
C10 H10 0.9300
C10 C9 1.357(5)
C10 C00F 1.336(6)
C7 H7 0.9300
C7 C00I 1.367(6)
C6 H6 0.9300
C6 C00B 1.413(5)
C6 C00K 1.465(6)
C9 C00D 1.449(6)
C9 C00E 1.487(6)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C8 C00C 1.595(5)
C00C C00G 1.545(5)
C00D H00D 0.9300
C00D C00L 1.395(6)
C00E H00A 0.9700
C00E H00B 0.9700
C00E C00G 1.399(6)
C00F H00F 0.9300
C00F C00M 1.459(5)
C00G H00G 0.9800
C00G C00H 1.553(6)
C00H H00C 0.9700
C00H H00E 0.9700
C00H C00J 1.553(6)
C00I H00I 0.9300
C00I C00K 1.457(6)
C00J H00H 0.9700
C00J H00J 0.9700
C00K H00K 0.9300
C00L H00L 0.9300
C00L C00M 1.423(6)
C00M H00M 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189024
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 -0.176 -0.761 1665.8 390.3
2 0.500 -0.393 -0.579 1665.8 390.3
