#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/14/4021482.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_4021482
loop_
_publ_author_name
'Fraser F. Fleming'
'Zhiyu Zhang'
'Guoqing Wei'
'Omar W. Steward'
_publ_contact_author_address
;
  Department of Chemistry and Biochemistry
  Duquesne University
  Pittsburgh, PA 15282 USA
;
_publ_contact_author_email       ' steward@duq.edu '
_publ_contact_author_fax         ' (412) 396 5683 '
_publ_contact_author_name        'Omar W. Steward'
_publ_contact_author_phone       ' (412) 396 6338 '
_publ_section_title
;
 C-Metalated Nitriles: Electrophile-Dependent Alkylations and Acylations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1430
_journal_page_last               1435
_journal_paper_doi               10.1021/jo052102j
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C21 H23 N O '
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.42
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             'Noc. 29, 2002'
_audit_creation_method           'by teXsan v1.8'
_audit_update_record             '6/2/05 update Omar W. Steward'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.422(5)
_cell_length_b                   16.648(6)
_cell_length_c                   6.804(3)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    298
_cell_measurement_theta_max      16.7
_cell_measurement_theta_min      15.1
_cell_volume                     1747(1)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_diffrn_ambient_temperature      298.2
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.04375
_diffrn_orient_matrix_UB_12      -0.03426
_diffrn_orient_matrix_UB_13      0.06914
_diffrn_orient_matrix_UB_21      -0.02014
_diffrn_orient_matrix_UB_22      -0.04780
_diffrn_orient_matrix_UB_23      -0.07637
_diffrn_orient_matrix_UB_31      0.04344
_diffrn_orient_matrix_UB_32      0.01226
_diffrn_orient_matrix_UB_33      -0.10486
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00000
_diffrn_reflns_av_sigmaI/netI    0.060
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2330
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0.02
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             656.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.439
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;'w = 1/[σ²(Fo) + 
.00040|Fo|²]'
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0487
_reflns_number_gt                1717
_reflns_number_total             2330
_reflns_threshold_expression     I>3.00σ(I)
_cod_data_source_file            jo052102jsi20051214_105650_06.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_A' replaced with
'_geom_hbond_atom_site_label_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C21 H23 N O '
_cod_database_code               4021482
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2-x,   -y,1/2+z'
'1/2+x,1/2-y,   -z'
'   -x,1/2+y,1/2-z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
O(1) 0.5591(1) 0.29139(9) 0.7154(3) 0.0466(5) 1.000 Uani d
N(1) 0.5035(2) -0.0354(1) 0.7957(4) 0.0634(8) 1.000 Uani d
C(1) 0.4876(2) 0.1208(1) 0.7572(4) 0.0355(6) 1.000 Uani d
C(2) 0.5641(2) 0.1615(1) 0.8735(4) 0.0362(6) 1.000 Uani d
C(3) 0.5519(2) 0.2532(1) 0.9037(4) 0.0422(7) 1.000 Uani d
C(4) 0.4629(2) 0.2708(2) 0.9920(5) 0.0515(8) 1.000 Uani d
C(5) 0.3900(2) 0.2338(2) 0.8757(5) 0.0506(8) 1.000 Uani d
C(6) 0.4015(2) 0.1436(2) 0.8577(4) 0.0447(7) 1.000 Uani d
C(7) 0.4980(2) 0.0323(1) 0.7799(4) 0.0427(7) 1.000 Uani d
C(8) 0.4873(2) 0.1380(2) 0.5320(4) 0.0415(7) 1.000 Uani d
C(9) 0.4134(2) 0.0998(1) 0.4205(4) 0.0395(7) 1.000 Uani d
C(10) 0.4217(2) 0.0246(2) 0.3340(4) 0.0485(8) 1.000 Uani d
C(11) 0.3523(2) -0.0093(2) 0.2311(4) 0.061(1) 1.000 Uani d
C(12) 0.2749(2) 0.0310(2) 0.2170(5) 0.063(1) 1.000 Uani d
C(13) 0.2660(2) 0.1045(2) 0.3018(5) 0.062(1) 1.000 Uani d
C(14) 0.3341(2) 0.1390(2) 0.3995(5) 0.0515(8) 1.000 Uani d
C(15) 0.6545(2) 0.1376(1) 0.8059(5) 0.0431(7) 1.000 Uani d
C(16) 0.6913(2) 0.1626(2) 0.6306(5) 0.0543(9) 1.000 Uani d
C(17) 0.7750(2) 0.1386(2) 0.5780(7) 0.074(1) 1.000 Uani d
C(18) 0.8227(2) 0.0907(2) 0.7041(9) 0.088(1) 1.000 Uani d
C(19) 0.7877(2) 0.0662(2) 0.8766(8) 0.085(1) 1.000 Uani d
C(20) 0.7039(2) 0.0890(2) 0.9284(6) 0.063(1) 1.000 Uani d
C(21) 0.6223(2) 0.2852(2) 1.0401(5) 0.061(1) 1.000 Uani d
H(1) 0.5587 0.1385 1.0030 0.041 1.000 Uiso c
H(2) 0.4606 0.2479 1.1218 0.068 1.000 Uiso c
H(3) 0.4549 0.3267 1.0007 0.068 1.000 Uiso c
H(4) 0.3357 0.2467 0.9360 0.060 1.000 Uiso c
H(5) 0.3899 0.2577 0.7459 0.060 1.000 Uiso c
H(6) 0.4006 0.1205 0.9875 0.054 1.000 Uiso c
H(7) 0.3542 0.1210 0.7852 0.054 1.000 Uiso c
H(8) 0.4847 0.1950 0.5141 0.053 1.000 Uiso c
H(9) 0.5407 0.1191 0.4779 0.053 1.000 Uiso c
H(10) 0.4753 -0.0044 0.3534 0.061 1.000 Uiso c
H(11) 0.3599 -0.0614 0.1652 0.077 1.000 Uiso c
H(12) 0.2287 0.0074 0.1399 0.081 1.000 Uiso c
H(13) 0.2099 0.1330 0.3029 0.077 1.000 Uiso c
H(14) 0.3287 0.1924 0.4527 0.059 1.000 Uiso c
H(15) 0.6581 0.1968 0.5420 0.068 1.000 Uiso c
H(16) 0.8020 0.1557 0.4611 0.088 1.000 Uiso c
H(17) 0.8792 0.0732 0.6601 0.103 1.000 Uiso c
H(18) 0.8237 0.0355 0.9625 0.095 1.000 Uiso c
H(19) 0.6790 0.0692 1.0511 0.082 1.000 Uiso c
H(20) 0.6782 0.2750 0.9904 0.082 1.000 Uiso c
H(21) 0.6178 0.2599 1.1690 0.082 1.000 Uiso c
H(22) 0.6154 0.3419 1.0607 0.082 1.000 Uiso c
H(23) 0.5424 0.3511 0.7331 0.083 1.000 Uiso c
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 84 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 92 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 4 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 4 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(3) O(1) H(23) 107.6 no
C(2) C(1) C(6) 108.5(2) yes
C(2) C(1) C(7) 107.0(2) yes
C(2) C(1) C(8) 114.7(2) yes
C(6) C(1) C(7) 106.8(2) yes
C(6) C(1) C(8) 112.8(2) yes
C(7) C(1) C(8) 106.5(2) yes
C(1) C(2) C(3) 113.5(2) yes
C(1) C(2) C(15) 115.0(2) yes
C(1) C(2) H(1) 103.0 no
C(3) C(2) C(15) 114.1(2) yes
C(3) C(2) H(1) 105.0 no
C(15) C(2) H(1) 104.6 no
O(1) C(3) C(2) 107.9(2) yes
O(1) C(3) C(4) 109.6(2) yes
O(1) C(3) C(21) 109.6(2) yes
C(2) C(3) C(4) 110.4(2) yes
C(2) C(3) C(21) 109.8(2) yes
C(4) C(3) C(21) 109.5(2) yes
C(3) C(4) C(5) 112.7(2) yes
C(3) C(4) H(2) 108.6 no
C(3) C(4) H(3) 109.4 no
C(5) C(4) H(2) 107.0 no
C(5) C(4) H(3) 109.9 no
H(2) C(4) H(3) 109.2 no
C(4) C(5) C(6) 111.1(2) yes
C(4) C(5) H(4) 109.7 no
C(4) C(5) H(5) 108.2 no
C(6) C(5) H(4) 111.1 no
C(6) C(5) H(5) 109.5 no
H(4) C(5) H(5) 107.3 no
C(1) C(6) C(5) 112.3(2) yes
C(1) C(6) H(6) 108.7 no
C(1) C(6) H(7) 109.4 no
C(5) C(6) H(6) 108.6 no
C(5) C(6) H(7) 109.9 no
H(6) C(6) H(7) 107.8 no
N(1) C(7) C(1) 178.0(3) yes
C(1) C(8) C(9) 114.8(2) yes
C(1) C(8) H(8) 107.8 no
C(1) C(8) H(9) 108.4 no
C(9) C(8) H(8) 108.8 no
C(9) C(8) H(9) 108.6 no
H(8) C(8) H(9) 108.2 no
C(8) C(9) C(10) 121.6(2) yes
C(8) C(9) C(14) 121.1(2) yes
C(10) C(9) C(14) 117.3(2) yes
C(9) C(10) C(11) 120.4(3) yes
C(9) C(10) H(10) 118.0 no
C(11) C(10) H(10) 121.5 no
C(10) C(11) C(12) 120.3(3) yes
C(10) C(11) H(11) 119.4 no
C(12) C(11) H(11) 120.2 no
C(11) C(12) C(13) 119.8(3) yes
C(11) C(12) H(12) 118.7 no
C(13) C(12) H(12) 121.4 no
C(12) C(13) C(14) 120.4(3) yes
C(12) C(13) H(13) 121.6 no
C(14) C(13) H(13) 117.8 no
C(9) C(14) C(13) 121.7(3) yes
C(9) C(14) H(14) 118.1 no
C(13) C(14) H(14) 120.1 no
C(2) C(15) C(16) 123.9(3) yes
C(2) C(15) C(20) 118.3(3) yes
C(16) C(15) C(20) 117.9(3) yes
C(15) C(16) C(17) 120.8(3) yes
C(15) C(16) H(15) 119.6 no
C(17) C(16) H(15) 119.6 no
C(16) C(17) C(18) 119.8(4) yes
C(16) C(17) H(16) 122.5 no
C(18) C(17) H(16) 117.6 no
C(17) C(18) C(19) 119.9(3) yes
C(17) C(18) H(17) 117.5 no
C(19) C(18) H(17) 122.5 no
C(18) C(19) C(20) 120.5(4) yes
C(18) C(19) H(18) 117.4 no
C(20) C(19) H(18) 122.1 no
C(15) C(20) C(19) 121.1(4) yes
C(15) C(20) H(19) 119.6 no
C(19) C(20) H(19) 119.4 no
C(3) C(21) H(20) 111.8 no
C(3) C(21) H(21) 110.2 no
C(3) C(21) H(22) 110.7 no
H(20) C(21) H(21) 108.1 no
H(20) C(21) H(22) 109.4 no
H(21) C(21) H(22) 106.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(3) 1.434(3) yes
O(1) H(23) 1.03 no
N(1) C(7) 1.135(3) yes
C(1) C(2) 1.573(3) yes
C(1) C(6) 1.541(4) yes
C(1) C(7) 1.491(3) yes
C(1) C(8) 1.559(4) yes
C(2) C(3) 1.553(3) yes
C(2) C(15) 1.521(4) yes
C(2) H(1) 0.96 no
C(3) C(4) 1.527(4) yes
C(3) C(21) 1.524(4) yes
C(4) C(5) 1.506(4) yes
C(4) H(2) 0.96 no
C(4) H(3) 0.94 no
C(5) C(6) 1.518(4) yes
C(5) H(4) 0.96 no
C(5) H(5) 0.97 no
C(6) H(6) 0.96 no
C(6) H(7) 0.96 no
C(8) C(9) 1.509(3) yes
C(8) H(8) 0.96 no
C(8) H(9) 0.96 no
C(9) C(10) 1.389(3) yes
C(9) C(14) 1.394(4) yes
C(10) C(11) 1.397(4) yes
C(10) H(10) 0.97 no
C(11) C(12) 1.372(5) yes
C(11) H(11) 0.98 no
C(12) C(13) 1.360(4) yes
C(12) H(12) 0.97 no
C(13) C(14) 1.370(4) yes
C(13) H(13) 0.99 no
C(14) H(14) 0.96 no
C(15) C(16) 1.385(4) yes
C(15) C(20) 1.389(4) yes
C(16) C(17) 1.398(4) yes
C(16) H(15) 0.97 no
C(17) C(18) 1.383(6) yes
C(17) H(16) 0.94 no
C(18) C(19) 1.355(6) yes
C(18) H(17) 0.97 no
C(19) C(20) 1.392(5) yes
C(19) H(18) 0.95 no
C(20) H(19) 0.98 no
C(21) H(20) 0.94 no
C(21) H(21) 0.98 no
C(21) H(22) 0.96 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) N(1) 3.042(3) 4_656 no
C(18) C(20) 3.554(5) 2_654 no
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
O(1) H(23) N(1) 1.034(2) 2.028(2) 3.042(2) 166.4(1) 4_656
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
_geom_torsion_publ_flag
O(1) C(3) C(2) C(1) -68.2(3) no
O(1) C(3) C(2) C(15) 66.2(3) no
O(1) C(3) C(4) C(5) 65.5(3) no
N(1) C(7) C(1) C(2) 161(10) no
N(1) C(7) C(1) C(6) 45(10) no
N(1) C(7) C(1) C(8) -76(10) no
C(1) C(2) C(3) C(4) 51.6(3) no
C(1) C(2) C(3) C(21) 172.5(2) no
C(1) C(2) C(15) C(16) 72.1(3) no
C(1) C(2) C(15) C(20) -109.2(3) no
C(1) C(6) C(5) C(4) -58.8(3) no
C(1) C(8) C(9) C(10) -92.3(3) no
C(1) C(8) C(9) C(14) 88.0(3) no
C(2) C(1) C(6) C(5) 55.3(3) no
C(2) C(1) C(8) C(9) -179.4(2) no
C(2) C(3) C(4) C(5) -53.3(3) no
C(2) C(15) C(16) C(17) 179.7(3) no
C(2) C(15) C(20) C(19) -178.8(3) no
C(3) C(2) C(1) C(6) -52.4(3) no
C(3) C(2) C(1) C(7) -167.3(2) no
C(3) C(2) C(1) C(8) 74.9(3) no
C(3) C(2) C(15) C(16) -61.6(3) no
C(3) C(2) C(15) C(20) 117.1(3) no
C(3) C(4) C(5) C(6) 57.2(3) no
C(4) C(3) C(2) C(15) -174.0(2) no
C(5) C(4) C(3) C(21) -174.3(2) no
C(5) C(6) C(1) C(7) 170.4(2) no
C(5) C(6) C(1) C(8) -73.0(3) no
C(6) C(1) C(2) C(15) 173.7(2) no
C(6) C(1) C(8) C(9) -54.4(3) no
C(7) C(1) C(2) C(15) 58.8(3) no
C(7) C(1) C(8) C(9) 62.5(3) no
C(8) C(1) C(2) C(15) -59.1(3) no
C(8) C(9) C(10) C(11) -179.8(3) no
C(8) C(9) C(14) C(13) -178.8(3) no
C(9) C(10) C(11) C(12) -1.0(4) no
C(9) C(14) C(13) C(12) -1.8(5) no
C(10) C(9) C(14) C(13) 1.5(4) no
C(10) C(11) C(12) C(13) 0.7(5) no
C(11) C(10) C(9) C(14) -0.1(4) no
C(11) C(12) C(13) C(14) 0.7(5) no
C(15) C(2) C(3) C(21) -53.2(3) no
C(15) C(16) C(17) C(18) -1.5(5) no
C(15) C(20) C(19) C(18) -0.5(5) no
C(16) C(15) C(20) C(19) 0.0(4) no
C(16) C(17) C(18) C(19) 1.1(5) no
C(17) C(16) C(15) C(20) 1.0(4) no
C(17) C(18) C(19) C(20) -0.1(6) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9791226
2 PubChem 11616477
