#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/98/2009807.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009807
loop_
_publ_author_name
'Rodier, N.'
'Babingui, J.-P.'
'Duflos, M.'
'LeBaut, G.'
_publ_section_title
N-(2,6-Diméthylphényl)-6-hydroxy-2,5,7,8-tétraméthyl-3,4-dihydro-2H-1-benzopyran-2-carboxamide
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              957
_journal_page_last               960
_journal_paper_doi               10.1107/S0108270193012107
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C22 H27 N O3'
_chemical_formula_weight         353.47
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 90.19(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            8
_cell_length_a                   21.502(6)
_cell_length_b                   8.590(2)
_cell_length_c                   21.188(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      11.59
_cell_measurement_theta_min      6.03
_cell_volume                     3913.4(16)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2722
_diffrn_reflns_theta_max         23
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blanche
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       '  approximativement parallélépipédique'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.19(4)
_refine_diff_density_min         -0.16(4)
_refine_ls_extinction_coef       'g = 2.9(6)x10^-7^'
_refine_ls_extinction_method     'Stout & Jensen (1968)'
_refine_ls_goodness_of_fit_obs   1.47
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     317
_refine_ls_number_reflns         1501
_refine_ls_R_factor_obs          0.051
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.050
_reflns_number_observed          1501
_reflns_number_total             2722
_reflns_observed_criterion       I>=1.5\s(I)
_cod_data_source_file            pa1073.cif
_cod_data_source_block           pa1073_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3913(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C22 H27 N1 O3'
_cod_database_code               2009807
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .33620(10) .1396(3) .08230(9)
C(2) .3090(2) .0010(4) .05580(10)
C(3) .3257(2) -.1396(4) .0960(2)
C(4) .3044(2) -.1186(5) .1641(2)
C(5) .3212(2) .0398(4) .18890(10)
C(6) .3242(2) .0699(5) .2543(2)
C(7) .3426(2) .2146(4) .27430(10)
C(8) .3579(2) .3333(4) .2325(2)
C(9) .3531(2) .3063(4) .1678(2)
C(10) .3357(2) .1592(4) .14800(10)
C(11) .3409(2) -.0200(4) -.00810(10)
N(12) .39860(10) .0366(4) -.01140(10)
C(13) .4383(2) .0217(5) -.0651(2)
C(14) .4521(2) .1540(5) -.0993(2)
C(15) .4918(2) .1396(7) -.1511(2)
C(16) .5151(2) -.0030(8) -.1672(2)
C(17) .5007(2) -.1326(7) -.1333(2)
C(18) .4626(2) -.1232(5) -.0800(2)
O(19) .31540(10) -.0932(3) -.05050(10)
C(20) .3655(2) .4307(5) .1195(2)
C(21) .3786(3) .4890(5) .2583(2)
O(22) .34710(10) .2531(3) .33770(10)
C(23) .3077(2) -.0576(5) .3007(2)
C(24) .2393(2) .0230(3) .0474(2)
C(25) .4470(2) -.2666(6) -.0417(2)
C(26) .4252(2) .3084(6) -.0825(2)
H(3) .374(2) -.159(4) .093(2)
H'(3) .304(2) -.232(5) .076(2)
H(4) .327(2) -.205(5) .192(2)
H'(4) .256(2) -.130(5) .167(2)
H(12) .410(2) .098(5) .022(2)
H(15) .500(2) .234(6) -.175(2)
H(16) .541(3) -.014(6) -.201(3)
H(17) .515(2) -.238(6) -.137(2)
H(20) .365(2) .394(5) .076(2)
H'(20) .352(2) .525(5) .128(2)
H"(20) .404(2) .477(5) .122(2)
H(21) .400(2) .569(4) .229(2)
H'(21) .354(2) .538(6) .275(2)
H"(21) .397(2) .482(6) .297(2)
H(22) .342(2) .188(5) .366(2)
H(23) .279(2) -.136(5) .284(2)
H'(23) .282(2) -.008(5) .337(2)
H"(23) .345(2) -.085(5) .324(2)
H(24) .224(2) .051(5) .086(2)
H'(24) .233(2) .124(5) .019(2)
H"(24) .223(2) -.071(5) .033(2)
H(25) .448(2) -.246(6) .004(2)
H'(25) .409(2) -.305(6) -.056(2)
H"(25) .480(2) -.355(6) -.049(2)
H(26) .440(2) .375(6) -.102(2)
H'(26) .386(2) .303(6) -.087(2)
H"(26) .429(2) .337(6) -.036(2)
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(2) O(1) C(10) 118.9(2) yes
O(1) C(2) C(3) 110.1(3) yes
O(1) C(2) C(11) 105.1(3) yes
O(1) C(2) C(24) 109.9(3) yes
C(3) C(2) C(11) 107.3(3) yes
C(3) C(2) C(24) 113.2(3) yes
C(11) C(2) C(24) 110.8(3) yes
C(2) C(3) C(4) 111.4(3) yes
C(3) C(4) C(5) 111.4(3) yes
C(4) C(5) C(6) 121.2(3) yes
C(4) C(5) C(10) 120.6(3) yes
C(6) C(5) C(10) 118.1(3) yes
C(5) C(6) C(7) 118.8(3) yes
C(5) C(6) C(23) 119.7(3) yes
C(7) C(6) C(23) 121.5(3) yes
C(6) C(7) C(8) 122.4(3) yes
C(6) C(7) O(22) 122.4(3) yes
C(8) C(7) O(22) 115.2(3) yes
C(7) C(8) C(9) 119.1(3) yes
C(7) C(8) C(21) 119.2(3) yes
C(9) C(8) C(21) 121.6(3) yes
C(8) C(9) C(10) 118.1(3) yes
C(8) C(9) C(20) 122.6(3) yes
C(10) C(9) C(20) 119.3(3) yes
O(1) C(10) C(5) 122.5(3) yes
O(1) C(10) C(9) 114.1(3) yes
C(5) C(10) C(9) 123.4(3) yes
C(2) C(11) N(12) 115.1(3) yes
C(2) C(11) O(19) 120.5(3) yes
N(12) C(11) O(19) 124.2(3) yes
C(11) N(12) C(13) 124.6(3) yes
N(12) C(13) C(14) 118.3(3) yes
N(12) C(13) C(18) 119.3(3) yes
C(14) C(13) C(18) 122.5(3) yes
C(13) C(14) C(15) 118.2(4) yes
C(13) C(14) C(26) 121.5(3) yes
C(15) C(14) C(26) 120.3(4) yes
C(14) C(15) C(16) 120.0(5) yes
C(15) C(16) C(17) 121.4(4) yes
C(16) C(17) C(18) 120.9(5) yes
C(13) C(18) C(17) 117.3(4) yes
C(13) C(18) C(25) 121.6(3) yes
C(17) C(18) C(25) 121.1(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.440(4) yes
O(1) C(10) 1.402(4) yes
C(2) C(3) 1.520(5) yes
C(2) C(11) 1.530(4) yes
C(2) C(24) 1.523(5) yes
C(3) C(4) 1.526(5) yes
C(4) C(5) 1.501(5) yes
C(5) C(6) 1.412(4) yes
C(5) C(10) 1.379(5) yes
C(6) C(7) 1.372(5) yes
C(6) C(23) 1.514(5) yes
C(7) C(8) 1.392(5) yes
C(7) O(22) 1.386(4) yes
C(8) C(9) 1.393(5) yes
C(8) C(21) 1.511(6) yes
C(9) C(10) 1.383(5) yes
C(9) C(20) 1.505(5) yes
C(11) N(12) 1.333(4) yes
C(11) O(19) 1.225(4) yes
N(12) C(13) 1.430(4) yes
C(13) C(14) 1.381(6) yes
C(13) C(18) 1.386(6) yes
C(14) C(15) 1.398(5) yes
C(14) C(26) 1.491(7) yes
C(15) C(16) 1.367(8) yes
C(16) C(17) 1.361(8) yes
C(17) C(18) 1.400(6) yes
C(18) C(25) 1.514(6) yes
C(3) H(3) 1.05(4) no
C(3) H'(3) 1.01(4) no
C(4) H(4) 1.06(4) no
C(4) H'(4) 1.04(4) no
N(12) H(12) .91(4) no
C(15) H(15) .97(5) no
C(16) H(16) .92(6) no
C(17) H(17) .96(5) no
C(20) H(20) .97(4) no
C(20) H'(20) .87(4) no
C(20) H"(20) .91(4) no
C(21) H(21) 1.02(5) no
C(21) H'(21) .76(5) no
C(21) H"(21) .91(5) no
O(22) H(22) .83(4) no
C(23) H(23) .98(4) no
C(23) H'(23) 1.04(4) no
C(23) H"(23) .97(4) no
C(24) H(24) .91(4) no
C(24) H'(24) 1.06(4) no
C(24) H"(24) .93(4) no
C(25) H(25) .98(5) no
C(25) H'(25) .93(5) no
C(25) H"(25) 1.05(5) no
C(26) H(26) .78(5) no
C(26) H'(26) .86(5) no
C(26) H"(26) 1.02(5) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139057198
